Hydrochloric Acid → HCID 117653197, compound

HRID 588395Notes

Reaction equation

HRID 588395 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]([C:32]2[N:33]=[CH:34][CH:35]=[C:36]3[CH:40]=[CH:39][N:38]([CH3:41])[C:37]=23)[C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[N:25][N:26]([CH3:31])[C:27]=3[C:28]([OH:30])=[O:29])=[CH:19][CH:18]=2)=[O:16])[CH2:9]1)=O)(C)(C)C.[ClH:42]>O1CCOCC1>[ClH:42].[CH3:31][N:26]1[C:27]([C:28]([OH:30])=[O:29])=[C:23]([C:20]2[CH:19]=[CH:18][C:17]([C:15](=[O:16])[N:14]([C:32]3[N:33]=[CH:34][CH:35]=[C:36]4[CH:40]=[CH:39][N:38]([CH3:41])[C:37]=34)[C@@H:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)=[CH:22][CH:21]=2)[CH:24]=[N:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117653190HCID 117653190, compound2×

Product 1

HCID 117653197HCID 117653197, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of the compound from Step 3 (R)-4-(4-((1-(tert-butoxycarbonyl)piperidin-3-yl)(1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)carbamoyl)phenyl)-1-methyl-1H-pyrazole-5-carboxylic acid (0.18 g, 0.17 mmol) in 1,4-dioxane (10 mL) was added HCl in 1,4-dioxane (10 mL, 4 N). The mixture was stirred at room temperature for 1 h. The mixture was concentrated in vacuo. The resulting residue was triturated with EtOAc to deliver the hydrochloride salt of the title compound (0.12 g, 70% over 2 steps) as a brown solid. 1H NMR (400 MHz, DMSO-d6, T=80° C.) δ 9.38 (br s, 1H), 9.11 (br s, 1H), 8.11 (d, 0.75H), 8.08 (d, 0.25H), 7.57 (d, 1H), 7.52-7.46 (m, 2H), 7.28-7.17 (m, 4H), 6.61 (d, 0.25H), 6.49 (d, 0.75H), 4.02 (s, 3H), 3.98-3.94 (m, 1H), 3.90 (s, 3H), 3.76-3.67 (m, 1H), 3.61-3.50 (m, 1H), 3.28-3.15 (m, 1H), 2.86-2.64 (m, 2H), 1.90-1.69 (m, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe resulting residue was triturated with EtOAc

Sources & evidence

ORD record
ord-24072a0ae2ca45d5a4f6f7fcc51700dc
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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