HCID 68725159, compound → HCID 178422912, compound

HRID 1042277Notes

Reaction equation

HRID 1042277 reaction equation
COC1C=CC(C[N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:17]2[C:18]([NH:23][C:24]3[C:25]([CH3:43])=[CH:26][CH:27]=[C:28]4[C:33]=3[N:32]=[CH:31][N:30]=[C:29]4[NH:34][C:35]3[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=CC=1>C(O)(C(F)(F)F)=O>[N:12]1[C:13]([C:17]2[C:18]([NH:23][C:24]3[C:25]([CH3:43])=[CH:26][CH:27]=[C:28]4[C:33]=3[N:32]=[CH:31][N:30]=[C:29]4[NH:34][C:35]3[CH:36]=[CH:37][C:38]([C:39]#[N:40])=[CH:41][CH:42]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:14]2[C:9]([NH:8][CH:16]=[N:15]2)=[N:10][CH:11]=1

Participants

3

Reactant 1

HCID 68725159HCID 68725159, compound

Product 1

HCID 178422912HCID 178422912, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(8-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile (91 mg, 154 μmol) in TFA (3 mL) was heated at 70° C. for 3 h. The TFA was removed in vacuo and 2M NH3/MeOH was added. The mixture was stirred for 5 min and solvent was removed in vacuo. The product was purified by flash chromatography eluting with MeOH(NH3)/DCM (2-6%) to give 4-(8-(3-(9H-purin-6-yl)pyridin-2-ylamino)-7-methylquinazolin-4-ylamino)benzonitrile. MS (ESI, pos. ion) m/z: 471.2 [M+H]+

Workup

  1. customThe TFA was removed in vacuo and 2M NH3/MeOH
  2. additionwas added
  3. customsolvent was removed in vacuo
  4. customThe product was purified by flash chromatography
  5. washeluting with MeOH(NH3)/DCM (2-6%)

Sources & evidence

ORD record
ord-61cf1a7a73304f0795512eed9f23518f
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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