HCID 131735685, compound → HCID 72944859, compound

HRID 531880Notes

Reaction equation

HRID 531880 reaction equation
[F:1][C:2]1[C:3]([NH:30]C(=O)OC(C)(C)C)=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:7]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:3]([NH2:30])=[N:4][CH:5]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 131735685HCID 131735685, compound

Product 1

HCID 72944859HCID 72944859, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl (3-fluoro-5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)carbamate (90 mg, 0.179 mmol) was deprotected in TFA (10 mL) to afford 15 mg (16.3% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.47 (s, 1H), 8.42-8.41 (d, 1H), 8.26-8.21 (m, 2H), 8.11-0.810 (d, 1H), 7.98 (s, 1H), 7.69 (s, 1H), 7.41-7.33 (m, 1H), 7.12-6.99 (m, 3H), 5.44 (s, 2H). MS: m/z=403.4 (M+1), HPLC: 97.56% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-4d82ff07da2649cbbb46215060ad601e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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