Hydrochloric Acid → HCID 178517426, compound

HRID 718635Notes

Reaction equation

HRID 718635 reaction equation
C([O:3][C:4]([O:6][NH:7][C:8](=[NH:42])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[N:20]=[CH:21][CH:22]=[C:23]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:18]3=[N:17][C:16]=2[C:30]#[C:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]=2)=[CH:11][N:10]=1)=O)C.N1CCCN2CCCCCC=12.Cl>CC1C=CC=CC=1C>[O:27]1[CH2:26][CH2:25][N:24]([C:23]2[C:18]3[N:19]([C:15]([C:12]4[CH:13]=[CH:14][C:9]([C:8]5[N:42]=[C:4]([OH:3])[O:6][N:7]=5)=[N:10][CH:11]=4)=[C:16]([C:30]#[C:31][C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[N:17]=3)[N:20]=[CH:21][CH:22]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178473665HCID 178473665, compound

Product 1

HCID 178517426HCID 178517426, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of compound 42b (0.10 g, 0.18 mmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.10 g, 0.66 mmol) in o-xylene (2 mL) was stirred at 130° C. in an oil bath for 2 h. The reaction mixture was allowed to cool to rt, and the solution was adjusted to pH 7 with 0.5 N HCl. The solids formed were collected by filtration and washed with CH2Cl2/MeOH (1:10) (3×10 mL) to obtain the title compound 26 as a brown solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 13.25 (s, 1H), 9.48 (s, 1H), 8.79-8.75 (m, 1H), 8.47 (d, J=8.4 Hz, 1H), 8.33 (d, J=5.7 Hz, 1H), 8.24 (d, J=8.7 Hz, 1H), 8.06-8.01 (m, 2H), 7.87-7.66 (m, 3H), 7.56 (d, J=6.0 Hz, 1H), 4.10-3.98 (m, 4H), 3.91-3.78 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H20N8O3: 517.2 (M+H). Found: 517.1.

Workup

  1. customThe solids formed
  2. filtrationwere collected by filtration
  3. washwashed with CH2Cl2/MeOH (1:10) (3×10 mL)

Sources & evidence

ORD record
ord-f48c6eed7a1140459a32567b484915ee
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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