Hydrochloric Acid → HCID 74983293, compound

HRID 1915956Notes

Reaction equation

HRID 1915956 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[CH2:46][C:35]2([CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36]2)[CH2:34][CH2:33][CH2:32]1)=[O:23])=O)(C)(C)C.ClCCl.Cl>CO.O1CCOCC1>[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][CH2:34][C:35]2([CH2:36][NH:37][CH2:38]2)[CH2:46]1)=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 86680154HCID 86680154, compound

Product 1

HCID 74983293HCID 74983293, compoundYield 147.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 8-[4-[[5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl]amino]-2-methyl-pyrazol-3-yl]-2,8-diazaspiro[3.5]nonane-2-carboxylate (336 mg, 0.51 mmol) was dissolved in methanol (2 mL) and dichloromethane (2 mL) before the addition of 4 M of hydrogen chloride in 1,4-Dioxane (2 mL). The solution was stirred at room temperature for 16 hr. After evaporation, a crude mixture as an off while solid (345 mg) was obtained. The crude mixture was purified by reverse phase HPLC to give 508 as a white solid (66 mg, 28%). 1H NMR (400 MHz, DMSO-d6) δ 8.70 (s, 1H), 7.55-7.45 (m, 4H), 7.26 (t, J=8.8 Hz, 2H), 3.66 (s, 3H), 3.54 (s, 1H), 3.22 (s, 4H), 3.12 (s, 2H), 2.94 (t, J=5.3 Hz, 2H), 1.68-1.60 (m, 2H), 1.58-1.50 (m, 2H). MS (ESI) m/z: 460.2 [M+H+].

Workup

  1. customAfter evaporation

Sources & evidence

ORD record
ord-82b62ddb0f1f47638d0b383061f2c31d
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

Loading…