4-Methylmorpholine → 4-amino-5-(4-amino-3-fluorophenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

HRID 2197526노트

반응식

HRID 2197526 반응식
[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:21])[CH:15]=3)[C:9]([C:11]([OH:13])=O)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[F:22][C:23]([F:27])([F:26])[CH2:24][NH2:25].N1C2C=CC=C(O[P+](N(C)C)(N(C)C)N(C)C)C=2N=N1.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([F:21])[CH:15]=3)[C:9]([C:11]([NH:25][CH2:24][C:23]([F:27])([F:26])[F:22])=[O:13])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 595491934-Amino-5-(4-amino-3-fluorophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acidHCID 178486078HCID 178486078, 화합물

생성물 1

HCID 595491724-amino-5-(4-amino-3-fluorophenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-amino-5-(4-amino-3-fluorophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (24.6 g, 85.6 mmol) was added to a mixture of 2,2,2-trifluoro-1-aminoethane (42.4 g, 428 mmol), benzotriazolyloxytris(dimethylamino)phosphonium PF6 (56.8 g, 128 mmol) and 4-methylmorpholine (43.3 g, 428 mmol) in DMF (500 mL). The reaction mixture was stirred at rt for 16 h. The resulting precipitate was isolated by filtration and then washed with acetone and diethyl ether to give the desired product (22 g, 70%); 1H NMR (300 MHz, DMSO-d6) δ 8.37 (dd, J=8.5, 8.5 Hz, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.92-8.03 (br s, 1H), 7.89 (s, 1H), 6.99 (dd, J=12.2, 1.8 Hz, 1H), 6.85 (dd, J=12.2, 1.8 Hz, 1H), 6.74-6.6.82 (m, 1H), 5.35 (s, 2H), 5.13-3.22 (br s, 1H), 3.87-4.01 (m, 2H); ES-MS m/z 369.2 (MH)+; HPLC RT (Method B) 2.05 min.

후처리

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with acetone and diethyl ether

출처 및 근거

ORD 기록
ord-5de83a4b89f8431c95ae6420c32dfb2e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338594B2

반응 노트

불러오는 중…