Hydrochloric Acid → HCID 86345242, compound

HRID 1504004Notes

Reaction equation

HRID 1504004 reaction equation
[C:1]([CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[C:7](=[C:8]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20][CH2:19]4)[N:9]=[CH:10][N:11]=3)[C:6]1=2)(=[O:3])[NH2:2].Cl.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:24][CH:21]1[CH2:22][CH2:23][CH:18]([O:17][C:8]2[N:9]=[CH:10][N:11]=[C:12]3[C:7]=2[C:6]2[C@@H:5]([CH2:4][C:1]([NH2:2])=[O:3])[CH2:16][CH2:15][C:14]=2[S:13]3)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86695161HCID 86695161, compound

Product 1

HCID 86345242HCID 86345242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-(4-[[(3R)-3-(carbamoylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (120 mg, 0.27 mmol, 1.00 equiv) in dichloromethane (15 mL) was added hydrochloric acid (conc.) (0.2 mL). The resulting solution was stirred for 1 h at room temperature. The pH value of the solution was adjusted to pH>8 with saturated sodium bicarbonate solution. The solids were collected by filtration and then washed with water and methanol. This afforded 33.2 mg (36%) of 2-[(3R)-12-[(4-aminocyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]acetamide as a white solid. 1H NMR (300 MHz, CD3OD, ppm): δ 1.32-1.46 (m, 2H), 1.61-1.70 (m, 2H), 1.98-2.03 (m, 2H), 2.17-2.30 (m, 4H), 2.62-2.74 (m, 1H), 2.82-3.20 (m, 4H), 2.72-3.80 (m, 1H), 5.23-5.31 (m, 1H), 8.42 (s, 1H).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with water and methanol

Sources & evidence

ORD record
ord-9a40ee5679f54e73818f71b8d9413258
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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