Lithium Hydroxide → HCID 69311851, compound

HRID 1947059Notes

Reaction equation

HRID 1947059 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]([C:28](=[O:30])[NH2:29])=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-]>C1COCC1>[C:28]([C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]3[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)[N:18]=2)[CH:20]=1)(=[O:30])[NH2:29]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 59743409HCID 59743409, compound

Product 1

HCID 69311851HCID 69311851, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[4-(3-Carbamoyl-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (1.397 g, 3.44 mmol) was dissolved in THF, and LiOH (3.4 mL, 1M aq) was added, and the mixture stirred at RT for 6 h, and additional aliquot of LiOH (6.8 mL) added, and the mixture stirred overnight. A light yellow solid formed in the flask. The mixture was concentrated in vacuo to remove THF, more was added, and the solid filtered off, washed with DCM and Et2O, and air-dried overnight to provide 4-[4-(3-carbamoyl-indol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid (1.15 g, 89% yield).

Workup

  1. stirringthe mixture stirred overnight
  2. customA light yellow solid formed in the flask
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove THF
  5. additionmore was added
  6. filtrationthe solid filtered off
  7. washwashed with DCM and Et2O
  8. customair-dried overnight

Sources & evidence

ORD record
ord-c280c59c831b434c839c502daf280d61
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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