4-Methylmorpholine → HCID 59232053, compound

HRID 1099276Notes

Reaction equation

HRID 1099276 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]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]=4)=[O:22])=[CH:16][CH:15]=3)[CH:9]=[C:10]([C:11](O)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.[F:34][C:35]([F:39])([F:38])[CH2:36][NH2:37].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[N:25]=4)=[O:22])=[CH:18][CH:19]=3)[CH:9]=[C:10]([C:11]([NH:37][CH2:36][C:35]([F:39])([F:38])[F:34])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59231993HCID 59231993, compound

Product 1

HCID 59232053HCID 59232053, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-5-{4-[({[6-(trifluoromethyl)pyridin-2-yl]amino}carbonyl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid (30.0 mg, 0.066 mmol), 2,2,2-trifluoroethylamine (32.5 mg, 0.33 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (58.0 mg, 0.13 mmol), and 4-methylmorpholine (13.3 mg, 0.13 mmol) in DMF (2 mL) was stirred at rt overnight. The crude reaction mixture was purified directly by HPLC using a gradient of 30-90% MeCN in water to afford 16.4 mg (36%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 9.88 (s, 1 H), 9.73 (s, 1 H), 9.40 (t, J=6.6 Hz, 1 H), 8.34 (bs, 1 H), 8.18 (s, 1 H), 8.05 to 7.98 (m, 2 H), 7.58 (d, J=8.6. Hz, 2 H), 7.51-7.49 (m, 1 H), 7.44 (d, J=8.7 Hz, 2 H), 7.24 (s, 1H), 5.94 (bs, 1 H), 4.33-4.24 (m, 2 H); MS [M+H]+=539.0; LCMS RT=3.24 min.

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly by HPLC

Sources & evidence

ORD record
ord-98375f7a97f74db0b85cf088beb12b22
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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