Triethylamine → HCID 59232202, compound

HRID 1099281Notes

Reaction equation

HRID 1099281 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH2:11][OH:12])[N:6]2[N:5]=[CH:4][N:3]=1.C1([O:26][C:27](=O)[NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[N:30]=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:13]3[CH:18]=[CH:17][C:16]([NH:19][C:27]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:36])[F:38])[N:30]=4)=[O:26])=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH2:11][OH:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59232105HCID 59232105, compoundHCID 67079715HCID 67079715, compound

Product 1

HCID 59232202HCID 59232202, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]methanol (170.0 mg, 0.67 mmol), phenyl[6-(trifluoromethyl)pyridin-2-yl]carbamate (281.9 mg, 1.00 mmol), and triethylamine (0.46 mL, 1.33 mmol) in DMF (5 mL) was stirred at rt for 3 d. The crude reaction mixture was purified directly by HPLC using a gradient of 20-90% MeCN in water to yield 21.1 mg (7%) of the title compound. 1H-NMR (DMSO-d6) 9.89 (bs, 1 H), 9.72 (bs, 1 H), 8.05-7.98 (m, 2 H), 7.89 (s, 1 H), 7.57 (d, J=8.6 Hz, 2 H), 7.51-7.49 (m, 1 H), 7.40 (d, J=8.6 Hz, 1 H), 6.64 (s, 1 H), 5.19 (t, J=5.7 Hz, 1 H), 4.74 (d, J=5.6 Hz, 3 H); MS [M+H]+=444.1; LCMS RT=2.63 min.

Workup

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

Sources & evidence

ORD record
ord-eb752f68ea61466298d47d1d8c7d5dab
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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