Trifluoroacetic acid → HCID 178519131, compound

HRID 1044374Notes

Reaction equation

HRID 1044374 reaction equation
[CH2:1]([CH2:7]Cl)[CH2:2][O:3][C:4](Cl)=[O:5].[NH2:9][C:10]1[CH:11]=[C:12]([Cl:34])[C:13]([N:16]2[CH2:33][CH2:32][CH2:31][C@@:18]3([C:22](=[O:23])[N:21]([C@H:24]4[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[CH2:17]2)=[N:14][CH:15]=1.O[C@H]1CC[C@H](N2CC[C@]3(CCCNC3)C2=O)CC1.CC(C)([O-])C.[K+].C(O)(C(F)(F)F)=O>CN(C)C1C=CN=CC=1.CN(C=O)C.O1CCCC1.CO>[Cl:34][C:12]1[C:13]([N:16]2[CH2:33][CH2:32][CH2:31][C@@:18]3([C:22](=[O:23])[N:21]([C@H:24]4[CH2:25][CH2:26][C@H:27]([OH:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[CH2:17]2)=[N:14][CH:15]=[C:10]([N:9]2[CH2:7][CH2:1][CH2:2][O:3][C:4]2=[O:5])[CH:11]=1

Participants

10

Reactant 5

HCID 6422Trifluoroacetic acidHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 23665647Potassium tert-butoxideHCID 178508030HCID 178508030, compoundHCID 178517864HCID 178517864, compound

Product 1

HCID 178519131HCID 178519131, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Chloropropyl chloridocarbonate (15.1 μL, 0.000125 mol) was added to a mixture of (5S)-7-(5-amino-3-chloropyridin-2-yl)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (37.89 mg, 0.0001000 mol, this compound was prepared by using procedures analogous to those described for the synthesis of example 105, step 1 starting from (5S)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one) and 4-dimethylaminopyridine (18.3 mg, 0.000150 mol) in DMF (1.00 mL). After stirring the mixture for 1 h, 1.0000 M of potassium tert-butoxide in tetrahydrofuran (0.375 mL) was added and the resultant mixture was stirred at rt for 2 h. The mixture was diluted with methanol (0.8 mL) and was adjusted to pH=2.0 with TFA. The resulting solution was purified by prep.-HPLC to give the desired product. LC-MS: 463.1 (M+H)+.

Workup

  1. customthis compound was prepared
  2. customThe resulting solution was purified by prep.-HPLC

Sources & evidence

ORD record
ord-dc9404790d594588835b2943a9ef7ac7
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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