Trifluoroacetic acid → HCID 58529336, compound

HRID 1972883Notes

Reaction equation

HRID 1972883 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18]3[N:26]4[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]4)=[C:20]([C:28]4[CH:29]=[CH:30][C:31]5[C:35]([CH:36]=4)=[N:34][N:33]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:32]=5)[CH:19]=3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:37]([N:33]1[CH:32]=[C:31]2[C:35]([CH:36]=[C:28]([C:20]3[CH:19]=[C:18]([C:12]4[CH:11]=[C:10]5[C:15]([CH2:16][CH2:17][NH:8][CH2:9]5)=[CH:14][CH:13]=4)[N:26]4[C:21]=3[C:22]([NH2:27])=[N:23][CH:24]=[N:25]4)[CH:29]=[CH:30]2)=[N:34]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58529337HCID 58529337, compound

Product 1

HCID 58529336HCID 58529336, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-[4-amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (2.7 g, 4.7 mmol) in DCM (17 mL) was added TFA (8.6 mL), and the reaction mixture was stirred at rt overnight. The reaction mixture was concentrated and ethyl acetate was added. Saturated, aqueous NaHCO3 was added until the pH was basic. Yellow gum formed in the wall of glass, it was dried in vacuum oven overnight and the title product was obtained as light yellow solid, 2.2 g (98%). 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1 H), 8.05 (d, 2 H), 8.0 (s, 1 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 7 H), 7.25 (d, 1 H), 7.20 (s, 1 H), 5.70 (s, 2 H), 4.1 (m, 2 H), 3.2 (m, 2 H), 2.80 (m, 2 H); ES-MS m/z 472.29 [M+H]+, HPLC RT (min) 2.22.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added
  3. additionSaturated, aqueous NaHCO3 was added until the pH
  4. customYellow gum formed in the wall of glass, it
  5. customwas dried in vacuum oven overnight

Sources & evidence

ORD record
ord-28992d55f81244968a5c108847f6b854
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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