Hydrochloric Acid → HCID 178521318, compound

HRID 870590Notes

Reaction equation

HRID 870590 reaction equation
Cl.[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[CH2:21][N:20]([C:22](=[O:39])[CH2:23][N:24]([CH2:32][CH2:33][C:34]3[N:35]=[N:36][NH:37][CH:38]=3)C(=O)OC(C)(C)C)[CH2:19][CH2:18][C:16]=2[N:17]=1>ClCCl.CO>[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[CH2:21][N:20]([C:22](=[O:39])[CH2:23][NH:24][CH2:32][CH2:33][C:34]3[N:35]=[N:36][NH:37][CH:38]=3)[CH2:19][CH2:18][C:16]=2[N:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178453339HCID 178453339, compound

Product 1

HCID 178521318HCID 178521318, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add hydrogen chloride (1M in ethyl ether; 2.55 mL; 8 equiv; 2.55 mmoles) to a 0° C. solution of tert-butyl {2-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-oxoethyl}[2-(1H-1,2,3-triazol-4-yl)ethyl]carbamate (0.165 g; 1.0 equiv; 0.318 mmoles) in dichloromethane (2 mL) and methanol (1 mL). After stirring for 1 hour at 0° C., concentrate the mixture. Redissolve the crude product in a 10:1 mixture of dichloromethane:methanol and wash with saturated sodium bicarbonate. Extract the aqueous layer with additional 10:1 mixtures of dichloromethane:methanol (4×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-2-{[2-(1H-1,2,3-triazol-4-yl)ethyl]amino}ethanone (0.136 g; 102%) as a brown foam: MS (m/z): 419 (M+1).

Workup

  1. concentrationconcentrate the mixture
  2. dissolutionRedissolve the crude product
  3. additionin a 10:1 mixture of dichloromethane
  4. washmethanol and wash with saturated sodium bicarbonate
  5. extractionExtract the aqueous layer with additional 10:1 mixtures of dichloromethane
  6. dry with materialDry the combined organic extracts over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-8663e2829e224704a19a0fcde14bc1ad
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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