Methylamine → HCID 58413339, compound

HRID 532275Notes

Reaction equation

HRID 532275 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([O:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[C:22]2[C:29]([CH3:30])=[C:28]([C:31](O)=[O:32])[S:27][C:23]=2[N:24]=[CH:25][N:26]=1)[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][N:35](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.CN>CN(C=O)C.C1COCC1.CO>[F:19][C:17]1[CH:16]=[CH:15][C:14]([NH:20][C:21]2[C:22]3[C:29]([CH3:30])=[C:28]([C:31](=[O:32])[NH:35][CH3:34])[S:27][C:23]=3[N:24]=[CH:25][N:26]=2)=[C:13]([CH:18]=1)[O:12][CH:10]([CH3:11])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58413372HCID 58413372, compound

Product 1

HCID 58413339HCID 58413339, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-(1-(tert-Butoxycarbonylamino)propan-2-yloxy)-4-fluorophenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylic acid (80 mg) in DMF (1 ml), TBTU (54 mg) and triethylamine (60 μl) were added. The mixture was stirred at room temperature for 5 min then methylamine in THF (2M; 420 μl) was added and the reaction stirred at room temperature overnight. The mixture was diluted with methanol and purified directly by RP-chromatography (water with 0.2% trifluoroacetic acid/methanol 72-100%) to give the title compound.

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. custompurified directly by RP-chromatography (water with 0.2% trifluoroacetic acid/methanol 72-100%)

Sources & evidence

ORD record
ord-4572f3f80f6f468393319a3e3cd92a2a
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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