HCID 178418863, compound → HCID 178418990, compound

HRID 1864605Notes

Reaction equation

HRID 1864605 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:25]=[C:24]([NH:26][C:27]3[NH:28][N:29]=[C:30]([CH3:32])[CH:31]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:11][CH:10]=1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:25]=[C:24]([NH:26][C:27]3[NH:28][N:29]=[C:30]([CH3:32])[CH:31]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 178418863HCID 178418863, compound

Product 1

HCID 178418990HCID 178418990, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of [2-(4-tert-Butoxycarbonylamino-phenylamino)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (IIc-60, 100 mg, 0.232 mmol) in a mixture of DCM/TFA (5/1, 12 mL) was stirred for 2 hours at room temperature. The solvents were removed in vacuo and the residue triturated in aqueous K2CO3. The resulting solid was collected by filtration and washed with diethyl ether to afford IIc-66 (69 mg, 90%) as an off-white solid, mp 164-167° C.; 1H NMR (DMSO) δ 2.24 (3H, s), 6.33 (1H, br s), 7.12 (2H, d), 7.48 (3H, m), 7.58 (1H, d), 7.86 (1H, t), 8.64 (1H, d), 10.86 (1H, br s), 11.46 (1H, s); IR (solid) 1681, 1512, 1496, 1433, 1415, 1187, 1129; MS 332.4 (M+H)+

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue triturated in aqueous K2CO3
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with diethyl ether
  5. customto afford IIc-66 (69 mg, 90%) as an off-white solid, mp 164-167° C.

Sources & evidence

ORD record
ord-853e90ff2d05445dba34045647c878f8
Source dataset
uspto-grants-2009_12
Patent number
US07625913B2

Reaction notes

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