Dimethylformamide → HCID 67205335, compound

HRID 387776Notes

Reaction equation

HRID 387776 reaction equation
C[N:2](C)C=O.C1(P(N=[N+]=[N-])([C:14]2[CH:19]=[CH:18]C=CC=2)=O)C=CC=CC=1.C[N:24]1[CH2:29][CH2:28]N[CH2:26][CH2:25]1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:59])[NH:39][C:40]2[CH:58]=[CH:57][C:43]([O:44][C:45]3[C:46]4[CH:53]=[C:52]([C:54]([OH:56])=O)[NH:51][C:47]=4[N:48]=[CH:49][N:50]=3)=[CH:42][CH:41]=2)=[CH:33][CH:32]=1>O.C(N(CC)CC)C>[CH2:25]([N:24]([CH2:29][CH3:28])[CH2:14][CH2:19][CH2:18][NH:2][C:54]([C:52]1[NH:51][C:47]2[N:48]=[CH:49][N:50]=[C:45]([O:44][C:43]3[CH:42]=[CH:41][C:40]([NH:39][C:38]([NH:37][C:34]4[CH:33]=[CH:32][C:31]([F:30])=[CH:36][CH:35]=4)=[O:59])=[CH:58][CH:57]=3)[C:46]=2[CH:53]=1)=[O:56])[CH3:26]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 531671-MethylpiperazineHCID 199401P,P-Diphenylphosphinic azideHCID 58931116HCID 58931116, compound

Product 1

HCID 67205335HCID 67205335, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

After adding 1 ml of dimethylformamide, 47 μl of triethylamine, 18.5 μl of diphenylphosphoryl azide and 8.2 μl of 1-methylpiperazine to 12 mg of the 4-{4-[3-(4-fluorophenyl)ureido]phenoxy)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid synthesized in Example 164, the mixture was stirred overnight at room temperature. Water was added, and the mixture was subjected to liquid separation and extraction with an ethyl acetate-tetrahydrofuran mixed solvent and to NH silica gel column chromatography (ethyl acetate-methanol) to obtain 27 mg of the title compound.

Workup

  1. customthe mixture was subjected to liquid separation and extraction with an ethyl acetate-tetrahydrofuran mixed solvent and to NH silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-be0e0616e3994f6fab63ef4e06cb94f5
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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