Water → 3-(4-Fluorobenzyl)-7-hydroxy-7,8,9,10-tetrahydropyrrolo[3',2':4,5]pyrido[2,3-c]azepin-6(3H)-one

HRID 640712Notes

Reaction equation

HRID 640712 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]4[C:20]([CH2:19][CH2:18][CH2:17][N:16]([O:21]C5CCCCO5)[C:15]4=[O:28])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.C1COCC1.O>C(O)(=O)C>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]4[C:20]([CH2:19][CH2:18][CH2:17][N:16]([OH:21])[C:15]4=[O:28])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 686651933-(4-Fluorobenzyl)-7-(tetrahydro-2H-pyran-2-yloxy)-7,8,9,10-tetrahydropyrrolo[3',2':4,5]pyrido[2,3-c]azepin-6(3H)-one

Product 1

HCID 115950103-(4-Fluorobenzyl)-7-hydroxy-7,8,9,10-tetrahydropyrrolo[3',2':4,5]pyrido[2,3-c]azepin-6(3H)-oneYield 61.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(4-fluorobenzyl)-7-(tetrahydro-2H-pyran-2-yloxy)-7,8,9,10 tetrahydropyrrolo[3′,2′:4,5]pyrido[2,3-c]azepin-6(3H)-one (18.53 mg, 0.045 mmol) was dissolved in acetic acid, THF and Water (3.5 ml, 5:1:1). The resulting mixture was stirred for 1 h at room temperature. The mixture was concentrated and purified by preparative HPLC to provide the title compound as a white powder (9.0 mg, 61% yield). 1H NMR (300 MHz, MeOH) □ ppm 8.57 (s, 1 H) 7.60 (d, J=3.20 Hz, 1 H) 7.11-7.20 (m, 2 H) 6.90-6.99 (m, 2 H) 6.72 (d, J=3.01 Hz, 1 H) 5.44 (s, 2 H) 3.51 (t, J=6.50 Hz, 2 H) 3.03 (t, J=7.16 Hz, 2 H) 2.14-2.25 (m, 2 H). LC-MS (APCl, M+H+): 329.1. HPLC: 98% purity.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4113e087dd564fd6970788b307d1929f
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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