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Ammonia → HCID 58413407, compound

HRID 532276
Notes
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Reaction equation

HRID 532276 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].C[N:35](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.N>CN(C=O)C>[C:31]([C:28]1[S:27][C:23]2[N:24]=[CH:25][N:26]=[C:21]([NH:20][C:14]3[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=3[O:12][CH:10]([CH3:11])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[C:22]=2[C:29]=1[CH3:30])(=[O:32])[NH2:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58413372HCID 58413372, compound

Product 1

HCID 58413407HCID 58413407, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

4-(2-(1-(tert-Butoxycarbonylamino)propan-2-yloxy)-4-fluorophenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (250 mg) and TBTU (170 mg) was dissolved in DMF (3 ml) and triethylamine (1900) was added. The mixture was stirred at room temperature for 10 min, then 0.5 ml conc. ammonia was added. The reaction was stirred for 2 h. Then the reaction mixture was concentrated in vacuo and purified by RP-chromatography (water with 0.2% trifluoroacetic acid/methanol 72-100%) to give the title compound.

Workup

  1. stirringThe reaction was stirred for 2 h
  2. concentrationThen the reaction mixture was concentrated in vacuo
  3. custompurified by RP-chromatography (water with 0.2% trifluoroacetic acid/methanol 72-100%)

Sources & evidence

ORD record
ord-5f5fdb4f717a456ba5800e619850974c
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853193B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes