1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44511937, 화합물

HRID 1782575노트

반응식

HRID 1782575 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 44511937HCID 44511937, 화합물수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

[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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bf83bf337f5742bfbdeac286f7db7407
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498346B2

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