Trifluoroacetic acid → [6-(3-Amino-prop-1-ynyl)-quinazolin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine

HRID 415025Notes

Reaction equation

HRID 415025 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=1)[N:26]=[CH:25]2)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]#[C:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=1)[N:26]=[CH:25]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66623769(3-{4-[1-(3-Fluoro-benzyl)-1H-indazol-5-ylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester

Product 1

HCID 66623580[6-(3-Amino-prop-1-ynyl)-quinazolin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amineYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-{4-[1-(3-Fluoro-benzyl)-1H-indazol-5-ylamino]-quinazolin-6-yl}-prop-2-ynyl)-carbamic acid tert-butyl ester (285 mg, 0.545 mmol) is suspended in DCM (6 ml) and TFA (6 ml) is added dropwise. The reaction is stirred at r.t. for 2 hours. The solvents are removed in a N2 stream, DCM (10 ml) is added, and the organic layer is treated with sat. aq. NaHCO3 and brine, dried, and concentrated to afford the pure product (197.6 mg, 86%).

Workup

  1. customThe solvents are removed in a N2 stream, DCM (10 ml)
  2. additionis added
  3. additionthe organic layer is treated with sat. aq. NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea695e572623411c86948d1f50114c72
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

Loading…