Hydrochloric Acid → HCID 5330302, compound

HRID 1271977Notes

Reaction equation

HRID 1271977 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[N:22]=[CH:21][C:20]([N:23]5[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)[N:14]=[CH:15][C:10]=3[C:9]([CH3:30])=[C:8]([C:31]([O:33]CC)=[CH2:32])[C:7]2=[O:36])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C(Cl)(Cl)Cl>[C:31]([C:8]1[C:7](=[O:36])[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:11]2[N:12]=[C:13]([NH:16][C:17]3[N:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[N:14]=[CH:15][C:10]=2[C:9]=1[CH3:30])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11202660HCID 11202660, compound

Product 1

HCID 5330302HCID 5330302, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8-cyclopentyl-6-(1-ethoxy-vinyl)-2-(4-hydroxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamino)-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (255 mg, 0.52 mmol) in chloroform (2 mL) was added hydrogen chloride (2 M ethereal solution, 5.0 mL, 10.0 mmol). The reaction mixture was stirred at RT for 12 h. The solvents were evaporated and the residue was dissolved in ethanol. The ethanol was evaporated to give 6-acetyl-8-cyclopentyl-2-(4-hydroxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamino)-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (213 mg, 0.46 mmol). MS (APCI+) 463 (M+1, 100); 1HNMR δ (400 MHz, DMSO-d6) 10.90 (br, 1H), 9.07 (s, 1H), 8.19 (s, 1H), 7.91 (br, 2H), 5.91–5.89 (m, 1H), 3.77 (br, 1H), 3.62 (br, 2H), 3.07 (br, 2H), 2.58 (s, 3H), 2.40 (s, 3H), 2.30 (br, 2H), 1.98–1.86 (m, 5H), 1.65 (br, 4H); Anal. Calc'd for C25H30N6O3, 1.76 C3H8O1, 0.36 CHCl3: C, 60.20; H, 7.33; N, 13.75. Found: C, 60.48; H, 6.97; N, 13.35.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in ethanol
  3. customThe ethanol was evaporated

Sources & evidence

ORD record
ord-9676362f2df84cd7a305a2731d8a0f18
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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