Isopropylamine → HCID 44511872, compound

HRID 1782564Notes

Reaction equation

HRID 1782564 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][C:40]=2[CH3:41])[CH:10]2[CH2:15][CH2:14][N:13]([C@H:16]([CH3:33])[CH2:17][CH2:18][NH:19][C:20](=[O:32])[C:21]3[C:29]([CH3:30])=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][C:22]=3[CH3:31])[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.C1C=C[C:56]2N(O)N=[N:59][C:57]=2[CH:58]=1.C(N)(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:57]([NH:59][C:25](=[O:26])[C:24]1[CH:28]=[C:29]([CH3:30])[C:21]([C:20]([NH:19][CH2:18][CH2:17][C@H:16]([N:13]2[CH2:12][CH2:11][CH:10]([N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][C:40]=3[CH3:41])[CH2:15][CH2:14]2)[CH3:33])=[O:32])=[C:22]([CH3:31])[CH:23]=1)([CH3:58])[CH3:56]

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68972272HCID 68972272, compound

Product 1

HCID 44511872HCID 44511872, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

N-((R)-3-{4-[(4-Methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-3,5-dimethyl-terephthalamic acid (0.050 g, 0.09 mmol), EDCI (0.019 g, 0.10 mmol) and HOBT (0.013 g, 0.10 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added isopropylamine (8 μL, 0.10 mmol) followed by DIPEA (19 μL, 0.11 mmol) and the resulting mixture was stirred at 25° C. for 16 h. Standard workup according to General Procedure C gave the crude product as a tan oil. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 93:5:2, v/v/v) afforded N′-isopropyl-N-((R)-3-{4-[(4-methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-2,6-dimethyl-terephthalamide (0.046 g, 86%) as a white foam. 1H NMR (CDCl3) δ 0.97 (d+m, 4H), 1.18 (d+m, 7H), 1.55 (m, 1H), 1.72 (m, 3H), 2.08 (br t, 1H), 2.26 (s, 6H), 2.30 (s, 3H), 2.42 (br t, 1H), 2.67-2.81 (m, 3H), 3.14 (m, 1H), 3.31 (m, 1H), 3.72 (s, 3H), 3.78 (m, 1H), 3.99 (s, 2H), 4.23 (m, 1H), 6.57 (d, 1H, J=6.0 Hz), 6.68 (d, 2H, J=9.0 Hz), 6.73 (d, 2H, J=9.0 Hz), 7.00 (d, 1H, J=3.0 Hz), 7.45 (s, 2H), 7.83 (s, 1H), 8.29 (s, 1H), 8.31 (d, 1H, J=6.0 Hz). 13C NMR (CDCl3) δ 13.7, 19.0, 19.6, 23.1, 29.7, 30.4, 31.3, 39.6, 42.2, 44.2, 47.7, 49.2, 51.9, 55.9, 59.6, 60.0, 114.8, 118.2, 121.4, 125.3, 126.5, 134.0, 134.8, 135.1, 141.2, 143.3, 145.2, 148.1, 149.4, 154.5, 166.5, 169.8. ES-MS m/z 600 (M+H). Anal. Calcd. for C36H49N5O3.0.1 CH2Cl2: C, 71.28; H, 8.15; N, 11.51. Found: C, 71.26; H, 8.18; N, 11.41.

Workup

  1. customto give a pale yellow solution
  2. customgave the crude product as a tan oil
  3. customPurification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 93:5:2, v/v/v)

Sources & evidence

ORD record
ord-8c143259a8be47e1b953409dffc4771d
Source dataset
uspto-grants-2009_03
Patent number
US07498346B2

Reaction notes

Loading…