Hydrochloric Acid → HCID 178517430, compound

HRID 1772598Notes

Reaction equation

HRID 1772598 reaction equation
C(O[C:4]([O:6][NH:7]/[C:8](=[N:42]/[H])/[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]3[CH:21]=[C:22]([CH:24]=[CH:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=[C:19]3[C:18]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[N:17][CH:16]=2)=[CH:11][N:10]=1)=[O:5])C.C1CCN2C(=NCCC2)CC1.O.Cl>CC1C=CC=CC=1C>[O:39]1[CH2:40][CH2:41][N:36]([C:18]2[C:19]3[N:20]([CH:21]=[C:22](/[CH:24]=[CH:25]/[C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=3)[C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]4[N:42]=[C:4]([OH:5])[O:6][N:7]=4)=[N:10][CH:11]=3)=[CH:16][N:17]=2)[CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178506524HCID 178506524, compound

Product 1

HCID 178517430HCID 178517430, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of compound 4b (200 mg, 0.350 mmol) in o-xylene (4 mL) was added DBU (300 mg, 1.97 mmol). The reaction mixture was stirred in a 10 mL sealed tube at 120° C. for 2 h. After cooling to rt, water (20 mL) was added, and the pH of the solution was adjusted to 7 using 1N HCl solution. The solids were collected by filtration and washed with DCM/MeOH (50:1 v/v, 3×10 mL) to obtain the title compound 95 as an orange solid (49.4 mg, 26% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 13.32 (s, 1H), 9.06 (s, 1H), 8.82-8.60 (m, 1H), 8.44-8.40 (m, 2H), 8.30-8.05 (m, 5H), 8.05-7.92 (m, 1H), 7.82 (s, 1H), 7.75 (d, J=9.9 Hz, 1H), 7.65 (s, 1H), 4.55-4.30 (m, 4H), 4.00-3.80 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H22N8O3: 519.2 (M+H). Found 519.2.

Workup

  1. customsealed tube at 120° C. for 2 h
  2. filtrationThe solids were collected by filtration
  3. washwashed with DCM/MeOH (50:1 v/v, 3×10 mL)

Sources & evidence

ORD record
ord-f8321e5a83fa4b53a9240e73a41c1399
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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