Hydrochloric Acid → HCID 90030698, compound

HRID 531526Notes

Reaction equation

HRID 531526 reaction equation
F[C:2]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([N:25]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1.[ClH:43].CCOCC>CO.O1CCOCC1>[ClH:43].[F:42][C:39]1[CH:38]=[C:3]([CH:2]=[CH:41][CH:40]=1)[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90031370HCID 90031370, compound

Product 1

HCID 90030698HCID 90030698, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (76 mg, 0.137 mmol) in methanol (5 ml) added saturated HCl in dioxane at 0° C. This gradually brought to RT and stirred for four hours. Reaction mass was cooled and added ether to get solids. Solvents decanted and solids washed by ethyl acetate and dried. This afforded 20 mg (29.8% yield) titled compound. 1H NMR (CD3OD, 400 MHz): δ 9.071-9.067 (d, 1H), 8.778-8.774 (d, 1H), 8.605 (s, 1H), 8.215 (s, 1H), 8.009 (s, 1H), 7.618-7.614 (m, 1H), 7.535-7.496 (t, 1H), 7.460-7.441 (m, 1H), 7.405-7.351 (m, 1H), 7.272-7.248 (m, 1H), 7.174-7.155 (m, 1H), 7.086-7.030 (m, 2H), 5.530 (s, 2H), 3.682-3.656 (m, 4H), 3.497-3.471 (m, 4H), 3.339 (s, 3H). MS: m/z=453.4 (M+1); HPLC: 89.28% in method A.

Workup

  1. customThis gradually brought to RT
  2. customReaction mass
  3. temperaturewas cooled
  4. customto get solids
  5. customSolvents decanted
  6. washsolids washed by ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-e1d5fd5d1dc143629fe928b1deda591b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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