Cyanamide → N-cyano-2-[4-[2-[(4-fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxamide

HRID 878716노트

반응식

HRID 878716 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:26])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][N:15]([C:17]3[CH:22]=[C:21]([C:23]([OH:25])=O)[CH:20]=[CH:19][N:18]=3)[CH:16]=2)=[CH:4][CH:3]=1.[N:27]#[C:28][NH2:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:28]([NH:29][C:23]([C:21]1[CH:20]=[CH:19][N:18]=[C:17]([N:15]2[CH:16]=[C:12]([CH2:11][CH2:10][N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH3:26])[CH:13]=[N:14]2)[CH:22]=1)=[O:25])#[N:27]

참가 물질

6

반응물 4

HCID 9864CyanamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867256662-[4-[2-[(4-Fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxylic acid

생성물 1

HCID 86725667N-cyano-2-[4-[2-[(4-fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxamide수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2-[4-[2-[(4-fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxylic acid (70 mg, 0.2 mmol), cyanamide (17 mg, 0.4 mmol), HATU (113 mg, 0.3 mmol) and DIEA (59 mg, 0.6 mmol) in DMF (3 mL) was stirred at room temperature for 3 hours. The mixture was concentrated and purified by prep-HPLC to give the compound (15 mg, 20%). 1H NMR (400 MHz, DMSO-d6): 2.67-2.74 (3H, m), 2.94-2.98 (2H, m), 3.28 (1H, m), 3.43-3.45 (1H, m), 4.26-4.30 (1H, m), 4.44-4.48 (1H, m), 7.31-7.36 (2H, m), 7.59-7.61 (2H, m), 7.70-7.71 (1H, m), 7.76 (1H, s), 8.31 (1H, s), 8.42 (1H, d, J=5.2 Hz), 8.58 (1H, s), 9.56 (1H, br). [M+H] Calc'd for C20H19FN6O, 379; Found, 379.

후처리

  1. concentrationThe mixture was concentrated
  2. custompurified by prep-HPLC

출처 및 근거

ORD 기록
ord-ba7237fafd1e4bc0937a7602a22503fa
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987461B2

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