Potassium sodium tartarate → HCID 178508589, compound

HRID 244185Notes

Reaction equation

HRID 244185 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH2:21])[C:15]=3[C:14]([C:22]3[CH:31]=[C:30]4[C:25]([CH:26]=[CH:27][C:28]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[N:29]4)=[CH:24][CH:23]=3)=[CH:13]2)[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(=O)C(C(C([O-])=O)O)O.[Na+].[K+]>C1COCC1>[NH2:21][C:20]1[C:15]2[C:14]([C:22]3[CH:31]=[C:30]4[C:25]([CH:26]=[CH:27][C:28]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[N:29]4)=[CH:24][CH:23]=3)=[CH:13][N:12]([C@@H:9]3[CH2:8][CH2:7][C@H:6]([CH2:4][OH:3])[CH2:11][CH2:10]3)[C:16]=2[N:17]=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 178472381HCID 178472381, compound

Product 1

HCID 178508589HCID 178508589, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into the THF (1 mL) solution of cis-4-[4-amino-5-(2-phenylquinolin-7-yl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclohexanecarboxylic acid ethyl ester (13.3 mg, 0.0271 mmol) was added dropwise LiAlH4 (1 M in THF, 203 μL, 0.75 eq.) at 0° C. under N2. After stirring at rt for 2 h, the reaction mixture was treated with saturated potassium sodium tartarate solution (5 mL) and extracted with EtOAc (2×10 mL). The extracts were washed with H2O (10 mL) and brine (10 mL), and dried over MgSO4. The drying agent was filtered off, and the filtrate was concentrated in vacuo. The crude material thus obtained was purified by preparative TLC (silica gel, eluting with 7% MeOH/CH2Cl2) to yield the title compound as beige powder. 1H NMR (CDCl3, 400 MHz): δ=1.77-2.02 (m, 9H), 3.77-3.78 (d, 2H, J=7.2 Hz), 4.77-4.82 (m, 1H), 5.30 (brs, 2H), 7.24 (s, 1H), 7.46-7.57 (m, 3H), 7.67-7.70 (dd, 1H, J=1.6 & 8.4 Hz), 7.89-7.93 (m, 2H), 8.18-8.20 (m, 2H), 8.25-8.28 (m, 2H), 8.36 (s, 1H). MS (ES+): 450.2 [MH+]. HPLC: tR=2.5 min (polar—5 min).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe extracts were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude material thus obtained
  7. customwas purified by preparative TLC (silica gel, eluting with 7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-53aad12361234f018665fa53e141c49d
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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