Hydrochloric Acid → HCID 72943514, compound

HRID 531533Notes

Reaction equation

HRID 531533 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([N:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)[CH:23]=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:8]([CH3:39])=[N:7]1.Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][CH:42]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:8]([CH3:39])=[N:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118524015HCID 118524015, compound

Product 1

HCID 72943514HCID 72943514, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(3-(3-(1-(3-fluorobenzyl)-3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (83 mg, 0.146 mmol) was deprotected in methanol (5 ml), HCl in dioaxane (5 ml). This afforded 20 mg (27.1% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.852-8.818 (m, 1H), 8.726-8.723 (d, 1H), 8.272 (s, 1H), 7.951 (s, 1H), 7.832-7.798 (d, 1H), 7.499-7.459 (t, 1H), 7.407-7.317 (m, 3H), 7.160-7.129 (m, 2H), 7.070-7.048 (m, 2H), 5.404 (s, 2H), 3.549-3.523 (m, 4H), 3.418-3.393 (m, 4H), 2.392 (s, 3H). MS: m/z=467.2 (M+1); HPLC: 94.845% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-b17d09f3f38848269d15c52fdc87e04a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…