Hydrochloric Acid → 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate hydrochloride

HRID 1055160Notes

Reaction equation

HRID 1055160 reaction equation
[ClH:1].[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[NH:11][C:12]1[N:13]=[CH:14][C:15]2[CH2:20][N:19]([C:21]([O:23][CH2:24][CH:25]3[CH2:30][N:29]4[CH:31]=[CH:32][N:33]=[C:28]4[CH2:27][CH2:26]3)=[O:22])[CH2:18][C:16]=2[N:17]=1>C(O)(C)C>[ClH:1].[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[NH:11][C:12]1[N:13]=[CH:14][C:15]2[CH2:20][N:19]([C:21]([O:23][CH2:24][CH:25]3[CH2:30][N:29]4[CH:31]=[CH:32][N:33]=[C:28]4[CH2:27][CH2:26]3)=[O:22])[CH2:18][C:16]=2[N:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 816898205,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate

Product 1

HCID 1317363435,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Add hydrogen chloride (1N, 0.62 mL; 1.05 equiv; 0.62 mmoles) to a solution of 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate isomer 2 (0.254 g; 1.00 equiv; 0.59 mmoles) in isopropyl alcohol (0.3 mL). Swirl the mixture until dissolution occurs, freeze the solution in a −78° C. dry ice bath, and lyophilize to afford 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethyl 2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate hydrochloride isomer 2 (0.28 g; 100%) as a brown foam. MS (m/z): 431(M+1).

Workup

  1. dissolutionSwirl the mixture until dissolution
  2. customin a −78° C.

Sources & evidence

ORD record
ord-bebb49af2c1f42ec8e929951fc4fc5e1
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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