Trifluoroacetic acid → N-[5-(6-benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine

HRID 19606

Reaction equation

HRID 19606 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]3[N:21]=[CH:22][CH:23]=[C:19]3[CH:18]=[C:17]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([O:34][CH2:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH:30]=4)[CH:25]=3)[N:16]=2)=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:35]([O:34][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([C:17]1[N:16]=[C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][CH:10]=3)[N:20]3[N:21]=[CH:22][CH:23]=[C:19]3[CH:18]=1)[CH:33]=[CH:32]2)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67319245{4-[5-(6-Benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenyl}-carbamic acid tert-butyl ester2×

Product 1

HCID 67318736N-[5-(6-benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of {4-[5-(6-benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenyl}-carbamic acid tert-butyl ester (compound C2)(450 mg), TFA (2 ml) and dichloromethane (10 ml) is stirred 4 h at ambient temperature. The reaction mixture is evaporated and coevaporated with toluene. The residue is partitioned between a aqueous saturated solution of sodium bicarbonate and ethyl acetate. After drying the organic phase is evaporated and the residue is dried in vacuum. A solid in quantitative yield is obtained.

Workup

  1. customThe reaction mixture is evaporated
  2. customThe residue is partitioned between a aqueous saturated solution of sodium bicarbonate and ethyl acetate
  3. customAfter drying the organic phase
  4. customis evaporated
  5. customthe residue is dried in vacuum
  6. customA solid in quantitative yield is obtained

Sources & evidence

ORD record
ord-92581b61ab5249748f5b0032e571d119
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Linked notes

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