Trifluoroacetic acid → HCID 178509776, compound

HRID 1819477Notes

Reaction equation

HRID 1819477 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][C:17]2[N:22]=[C:21]([NH:23][CH2:24][CH:25]3[CH2:30][CH2:29][CH:28]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[CH2:27][CH2:26]3)[C:20]([N+:36]([O-:38])=[O:37])=[CH:19][N:18]=2)[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH2:15][NH:16][C:17]1[N:22]=[C:21]([NH:23][CH2:24][C@H:25]2[CH2:26][CH2:27][C@H:28]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:29][CH2:30]2)[C:20]([N+:36]([O-:38])=[O:37])=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57885727[3-({5-Nitro-4-[(4-pyrrolidin-1-yl-cyclohexylmethyl)amino]-pyrimidin-2-ylamino}-methyl)-benzyl]-carbamic acid tert-butyl ester

Product 1

HCID 178509776HCID 178509776, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-({5-nitro-4-[(4-pyrrolidin-1-yl-cyclohexylmethyl)-amino]-pyrimidin-2-ylamino}-methyl)-benzyl]-carbamic acid tert-butyl ester (132 mg, 0.25 mmol) in DCM (1 mL) was added TFA (2 mL). After 20 min the reaction mixture was concentrated in vacuo and the resulting oil taken up in EtOAc and the solution washed with sat. NaHCO3. The aqueous layer was then extracted with 90:10 CHCl3/i-PrOH. The combined organic layers were concentrated in vacuo and the residue purified by column chromatography (silica gel, 96:4 to 93:7 DCM/10% NH4OH in MeOH) to afford the title compound (25 mg), m/z 440 (M+1)+.

Workup

  1. concentrationAfter 20 min the reaction mixture was concentrated in vacuo
  2. washthe solution washed with sat. NaHCO3
  3. extractionThe aqueous layer was then extracted with 90:10 CHCl3/i-PrOH
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customthe residue purified by column chromatography (silica gel, 96:4 to 93:7 DCM/10% NH4OH in MeOH)

Sources & evidence

ORD record
ord-05f02b4405c04d03ae60ed316d060e8a
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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