Hydrochloric Acid → HCID 67056679, compound

HRID 459567Notes

Reaction equation

HRID 459567 reaction equation
C(OC([NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([C:20]([NH:22][C@@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]3[NH:29][C:30]([C:32]3[NH:33][C:34]4[C:39]([CH:40]=3)=[CH:38][C:37]([Cl:41])=[CH:36][CH:35]=4)=[O:31])=[O:21])[S:19][C:13]=2[CH2:12]1)=O)(C)(C)C.C(O)C.Cl>ClCCl>[ClH:41].[NH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([C:20]([NH:22][C@@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]3[NH:29][C:30]([C:32]3[NH:33][C:34]4[C:39]([CH:40]=3)=[CH:38][C:37]([Cl:41])=[CH:36][CH:35]=4)=[O:31])=[O:21])[S:19][C:13]=2[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 58822122(+/-)-cis-N1-[[5-[2-(tert-Butoxycarbonylamino)-ethyl]-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl]carbonyl]-N 2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine

Product 1

HCID 67056679HCID 67056679, compoundYield 182.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-cis-N1-[[5-[2-(tert-Butoxycarbonylamino)-ethyl]-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl]carbonyl]-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine (450 mg) was dissolved in dichloromethane (5 ml), and a saturated ethanol solution (30 ml) of hydrochloric acid was added to stir the mixture at room temperature for 1 minute. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and solids deposited were collected by filtration to obtain the title compound (367 mg) as a pale yellow amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue, and solids
  3. filtrationdeposited were collected by filtration

Sources & evidence

ORD record
ord-444d4d7657224b7fa0e9f2e2818ee81b
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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