Tert-Butylamine → HCID 178449380, compound

HRID 2197533Notes

Reaction equation

HRID 2197533 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[NH:25][C:24]5[C:26]([F:31])=[CH:27][C:28]([F:30])=[CH:29][C:23]=5[N:22]=4)=[CH:16][CH:15]=3)[C:9]([C:11](O)=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[C:32]([NH2:36])([CH3:35])([CH3:34])[CH3:33].CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[NH:25][C:24]5[C:26]([F:31])=[CH:27][C:28]([F:30])=[CH:29][C:23]=5[N:22]=4)=[CH:16][CH:15]=3)[C:9]([C:11]([NH:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 79724-MethylmorpholineHCID 178508831HCID 178508831, compound

Product 1

HCID 178449380HCID 178449380, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (75.0 mg, 0.178 mmol) in DMF (3 mL) was added tert-butylamine (0.021 ml, 0.196 mmol), benzotriazolyloxytris(dimethlyamino)phosphonium PF6 (86.6 mg, 0.196 mmol), and 4-methylmorpholine (0.039 ml, 0.356 mmol). The reaction was stirred for 3 hr at rt and then purified directly by HPLC using 25-85% acetonitrile in water to afford the desired product (75.3 mg, 89%). 1H-NMR (300 MHz, DMSO-d6) δ 9.80 (s, 1H), 8.02 (s, 1H), 7.80-8.02 (m, 3H), 7.38 (dd, J=6.7, 2.0 Hz, 2H), 7.00 (dd, J=8.9, 2.2 Hz, 1H), 6.85 (ddd, J=10.7, 10.7, 2.4 Hz, 1H), 6.54 (s, 1H), 4.96-5.21 (br s, 1H), 1.16 (s, 9H); ES-MS m/z 477.1 (MH)+; HPLC RT (Method B) 2.54 min.

Workup

  1. custompurified directly by HPLC

Sources & evidence

ORD record
ord-f637eafa31b84842ad221da01faf7d39
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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