Ethanol → HCID 131727600, compound

HRID 729744Notes

Reaction equation

HRID 729744 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:7]1[C:8]([NH:29][CH2:30][C@@H:31]([C:43]([OH:45])=[O:44])[NH:32][C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])=[N:9][CH:10]=[N:11][C:12]=1[N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[N:28]=[C:27]3[C:22]([CH2:23][CH2:24][CH2:25][NH:26]3)=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)[CH3:6].[CH2:46](O)[CH3:47]>>[ClH:3].[ClH:3].[CH2:5]([C:7]1[C:8]([NH:29][CH2:30][C@@H:31]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[NH:32][C:33]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])=[N:9][CH:10]=[N:11][C:12]=1[N:13]1[CH2:14][CH2:15][CH:16]([C:19]2[N:28]=[C:27]3[C:22]([CH2:23][CH2:24][CH2:25][NH:26]3)=[CH:21][CH:20]=2)[CH2:17][CH2:18]1)[CH3:6]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 24386Thionyl ChlorideHCID 12094341HCID 12094341, compound

Product 1

HCID 131727600HCID 131727600, compoundYield 95%

Conditions

Temperature
-12 °C

Procedure

160 μl (2.19 mmoles) of thionyl chloride is added to 4 ml of ethanol cooled down to −12° C. under a nitrogen atmosphere and the mixture is stirred for 30 minutes. Then a solution of 354 mg (0.45 mmoles) of 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-[(phenylmethoxy)carbonyl]alanine, bis(trifluoroacetate) in 13 ml of ethanol is added. The mixture is stirred for 30 minutes at −12° C. then left to return to ambient temperature and finally heated at 40° C. for 4 hours under nitrogen. The reaction medium is evaporated to dryness under vacuum and the residue crystallizes from a mixture of diisopropyl ether and of pentane and the solid is filtered. 284 mg (Yield=95%) of expected product is obtained in the form of an amorphous beige solid.

Workup

  1. stirringThe mixture is stirred for 30 minutes at −12° C.
  2. waitthen left
  3. customto return to ambient temperature
  4. temperaturefinally heated at 40° C. for 4 hours under nitrogen
  5. customThe reaction medium is evaporated to dryness under vacuum
  6. customthe residue crystallizes from a mixture of diisopropyl ether and of pentane
  7. filtrationthe solid is filtered

Sources & evidence

ORD record
ord-703734797f4a4b2ab87a01193732dc21
Source dataset
uspto-grants-2009_09
Patent number
US07582640B2

Reaction notes

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