Hydrochloric Acid → HCID 67056679, compound

HRID 546515Notes

Reaction equation

HRID 546515 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-c4cc78300f71488c9d66a0ff6bfd8580
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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