Trifluoroacetic acid → 4-(3-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoic acid

HRID 1410003Notes

Reaction equation

HRID 1410003 reaction equation
C([O:5][C:6](=[O:42])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:41])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[N:22]=[C:23]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=4)[C:24]4[N:29]=[CH:28][S:27][C:25]=4[N:26]=3)[CH:16]=2)=[CH:9][CH:8]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([NH:30][C:23]2[C:24]3[N:29]=[CH:28][S:27][C:25]=3[N:26]=[C:21]([C:17]3[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=3)[C:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:42])=[O:5])=[CH:8][CH:9]=3)=[O:41])[N:22]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68379374Tert-butyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoate

Product 1

HCID 602039014-(3-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoic acidYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl-4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoate (45 mg, 0.077 mmol) in 10 mL of DCM was treated with TFA (2 mL) dropwise. The resulting yellow solution was stirred at ambient temperature overnight. The excess of solvent was removed under reduced pressure, the residue was triturated with n-hexane decanted, and dried to give 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)benzoic acid (27 mg, 66.4%). 1H NMR (300 MHz, DMSO): δ 12.80 (brs, 1H), 10.76 (s, 1H), 10.19 (s, 1H), 9.41 (s, 1H), 8.96 (s, 1H), 8.62 (d, 1H, J=7.8 Hz), 8.09 (d, 1H, J=7.8 Hz), 7.97 (s, 4H), 7.84 (s, 1H), 7.71 (t, 1H, J=7.7 Hz), 7.54 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 6.99 (d, 1H, J=8.7 Hz), 3.81 (s, 3H), 3.74 (s, 3H). LC-MS: 528 [M+H]+, tR=1.54 min. HPLC: 96.02% at 214 nm, 95.94% at 254 nm, tR=6.62 min.

Workup

  1. customThe excess of solvent was removed under reduced pressure
  2. customthe residue was triturated with n-hexane
  3. customdecanted
  4. customdried

Sources & evidence

ORD record
ord-e151ef827cf04eb7952ededeb59ce4af
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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