1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68775300, compound

HRID 1711158Notes

Reaction equation

HRID 1711158 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:18][C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[C:13]([NH:15]OC)=[O:14])[CH2:8][CH2:7]1)[CH3:5].[CH3:24]CN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:45]([C:47]1[CH:55]=[C:54]([CH3:56])[C:50]([C:51](O)=[O:52])=[C:49]([CH3:57])[N:48]=1)#[N:46].CCN(C(C)C)C(C)C>CN(C=O)C>[C:45]([C:47]1[CH:55]=[C:54]([CH3:56])[C:50]([C:51]([NH:1][CH2:2][CH2:3][CH:4]([N:6]2[CH2:7][CH2:8][CH:9]([N:12]([CH2:18][C:19]3[CH:23]=[CH:22][S:21][CH:20]=3)[C:13]([NH:15][CH3:24])=[O:14])[CH2:10][CH2:11]2)[CH3:5])=[O:52])=[C:49]([CH3:57])[N:48]=1)#[N:46]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 574315506-cyano-2,4-dimethyl-3-PyridinecarboxylicacidHCID 72290768HCID 72290768, compound

Product 1

HCID 68775300HCID 68775300, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-3-methoxy-1-thiophen-3-ylmethyl-urea (0.150 g, 0.44 mmol), EDCI (0.093 g, 0.48 mmol) and HOBt (0.066 g, 0.48 mmol) were combined in DMF (8 ml) to give a pale yellow solution. To this solution was added 6-cyano-2,4-dimethyl-nicotinic acid (0.091 g, 0.48 mmol) followed by DIPEA (126 μL, 0.66 mmol) and the resulting mixture was stirred at 25° C. for 16 h. Standard workup according to general procedure E gave the crude product as a tan oil. Purification by column chromatography on silica gel (Et2O:MeOH:NH4OH, 90:8:2, v/v/v) afforded 6-cyano-2,4-dimethyl-N-{3-[4-(3-methyl-1-thiophen-3-ylmethyl-ureido)-piperidin-1-yl]-butyl}-nicotinamide (0.170 g, 77%) as a white foam. 1H NMR (CDCl3) δ 0.95 (m, 1H), 1.03 (d+m, 4H), 1.48 (m, 1H), 1.56-1.73 (m, 5H), 2.22 (br t, 1H), 2.32 (s, 3H), 2.54 (s, 3H), 2.58 (br t, 1H), 2.71-2.85 (m, 3H), 3.31 (m, 1H), 3.62 (s, 1H), 3.66 (m, 1H), 3.75 (s, 2H), 3.86 (m, 1H), 4.21 (m, 1H), 7.00 (m, 2H), 7.14 (s, 1H), 7.21 (s, 1H), 7.41 (m, 1H), 8.75 (br d, 1H); ES-MS m/z 499 (M+H).

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 (Et2O:MeOH:NH4OH, 90:8:2, v/v/v)

Sources & evidence

ORD record
ord-97f0c4e5a18a4facb8432b44fe8f0f79
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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