Triethylamine → HCID 59232106, compound

HRID 1099274Notes

Reaction equation

HRID 1099274 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.C1([O:31][C:32](=O)[NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[N:35]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:32]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:41])[F:43])[N:35]=4)=[O:31])=[CH:22][CH:23]=3)[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59231994HCID 59231994, compoundHCID 67079715HCID 67079715, compound

Product 1

HCID 59232106HCID 59232106, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of butyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate (118.0 mg, 0.36 mmol) in DMF (3.5 mL) was added phenyl[6-(trifluoromethyl)pyridin-2-yl]carbamate (153.5 mg, 0.54 mmol), followed by triethylamine (0.10 mL, 0.73 mmol). The solution was stirred at rt overnight and then purified directly by HPLC using a gradient of 50-80% MeCN in water to yield 107.7 mg (58%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 9.88 (s, 1 H), 9.73 (s, 1 H), 8.08 (s, 1 H), 8.04 to 7.97 (m, 2 H), 7.58 (d, J=8.6 Hz, 2 H), 7.51 to 7.49 (m, 1 H), 7.44 (d, J=8.5 Hz, 2 H), 7.22 (s, 1 H), 4.26 (t, J=6.6 Hz, 2 H), 1.71-1.64 (m, 2 H), 1.47-1.38 (m, 2 H), 0.93 (t, J=7.3, 3 H); MS [M+H]+=514.2; LCMS RT=3.49 min.

Workup

  1. custompurified directly by HPLC

Sources & evidence

ORD record
ord-d0fc13ef8ddf415c93ff8027e8f0ffdf
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

Loading…