1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44511937、化合物

HRID 1782575ノート

反応式

HRID 1782575 の反応式
[NH2:1][CH2:2][CH2:3][C@H:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][C:29]=2[CH3:30])[C:13]2[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)[CH3:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[Cl:53][C:54]1[CH:62]=[C:61]([CH3:63])[C:57]([C:58](O)=[O:59])=[C:56]([CH3:64])[N:55]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:53][C:54]1[CH:62]=[C:61]([CH3:63])[C:57]([C:58]([NH:1][CH2:2][CH2:3][C@H:4]([N:6]2[CH2:11][CH2:10][CH:9]([N:12]([CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][C:29]=3[CH3:30])[C:13]3[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)[CH2:8][CH2:7]2)[CH3:5])=[O:59])=[C:56]([CH3:64])[N:55]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68971363HCID 68971363、化合物HCID 717213646-Chloro-2,4-dimethylpyridine-3-carboxylic acid--hydrogen chloride (1/1)

生成物 1

HCID 44511937HCID 44511937、化合物収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

[1-((R)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-(6-trifluoromethyl-pyridin-3-yl)-amine (72.9 mg, 0.17 mmol), EDCI (36.4 mg, 0.19 mmol) and HOBT (25.7 mg, 0.19 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 6-chloro-2,4-dimethyl-nicotinic acid hydrochloride salt (42.2 mg, 0.19 mmol) followed by DIPEA (66.3 μL, 0.38 mmol) and the resulting mixture was stirred at room temperature for 16 h. Standard workup according to General Procedure C gave the crude product as a tan oil. Purification by preparative TLC (91:8:1, CH2Cl2/MeOH/NH4OH) afforded 6-chloro-2,4-dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-(6-trifluoromethyl-pyridin-3-yl)-amino]-piperidin-1-yl}-butyl)-nicotinamide as a white foam (61.1 mg, 60%). 1H NMR (CDCl3) δ 1.03 (d, 3H, J=5 Hz), 1.23 (m, 1H), 1.40 (m, 1H), 1.65 (m, 3H), 1.76 (m, 1H), 1.91 (d, 2H, J=11 Hz), 2.24 (m, 1H), 2.30 (s, 3H), 2.41 (s, 3H), 2.51 (s, 3H), 2.61 (m, 1H), 2.85 (m, 3H), 3.40 (m 1H), 3.48 (s, 1H), 3.74 (m, 2H), 4.25 (s, 2H), 6.84 (dd, 1H, J=3 Hz, 9 Hz), 6.99 (s, 1H), 7.13 (d, 1H, J=5 Hz), 7.41 (m, 2H), 8.05 (d, 1H, J=3 Hz), 8.17 (s, 1H), 8.38 (d, 1H, J=5 Hz). ES-MS m/z 589 (M+H), 612 (M+Na). Anal. Calcd. For C30H36ClF3N6O: C, 61.17; H, 6.16; Cl, 6.02; F, 9.67; N, 14.27.

後処理

  1. customto give a pale yellow solution
  2. customgave the crude product as a tan oil
  3. customPurification by preparative TLC (91:8:1, CH2Cl2/MeOH/NH4OH)

出典と根拠

ORDレコード
ord-bf83bf337f5742bfbdeac286f7db7407
出典データセット
uspto-grants-2009_03
特許番号
US07498346B2

反応ノート

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