Hydrochloric Acid → HCID 74983286, compound

HRID 1915951Notes

Reaction equation

HRID 1915951 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[CH:29]=[N:28][N:27]([CH3:30])[C:26]=1[N:31]1[CH2:37][CH2:36][C:35]([O:39][CH3:40])([CH3:38])[CH:34]([NH:41]C(=O)OC(C)(C)C)[CH2:33][CH2:32]1)=[O:23])=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[CH:29]=[N:28][N:27]([CH3:30])[C:26]=1[N:31]1[CH2:32][CH2:33][CH:34]([NH2:41])[C:35]([O:39][CH3:40])([CH3:38])[CH2:36][CH2:37]1)=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86680148HCID 86680148, compound

Product 1

HCID 74983286HCID 74983286, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-(1-(4-((5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl)amino)-2-methyl-pyrazol-3-yl)-5-methoxy-5-methyl-azepan-4-yl]carbamate (0.12 g, 0.17 mmol) in MeOH (10 mL) was added HCl in dioxane (4 M, 10 mL, 0.04 mol). The reaction mixture was stirred at room temperature for 16 hr and concentrated under reduced pressure. Purification via preparative HPLC gave 485 as a pale yellow solid (64 mg, 74%). 1H NMR (400 MHz, d6-DMSO) δ 9.63 (s, 1H), 7.69 (s, 1H), 7.59-7.48 (m, 3H), 7.31-7.22 (m, 2H), 3.61 (s, 3H), 3.31-3.25 (m, 1H), 3.14-3.03 (m, 2H), 3.03 (s, 3H), 2.99-2.89 (m, 1H), 2.11-2.02 (m, 1H), 1.92-1.82 (m, 1H), 1.79-1.59 (m, 4H), 1.47 (dd, J=14.5, 6.2 Hz, 1H), 1.19 (s, 3H). LCMS (ES+) m/z 492 (M+1)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification via preparative HPLC

Sources & evidence

ORD record
ord-8f40e98f0f144f14a98481ac89beb25f
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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