Water → HCID 86345983, compound

HRID 1772599Notes

Reaction equation

HRID 1772599 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:24]=[C:25]([CH:27]=[CH:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[N:26]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16](/[C:19](=[N:22]\[H])/[NH:20][NH2:21])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.O.[C:40]([O-])(O)=O.[Na+]>C(O)=O>[N:21]1[NH:20][C:19]([C:16]2[N:17]=[CH:18][C:13]([C:10]3[N:9]4[CH:24]=[C:25](/[CH:27]=[CH:28]/[C:29]5[CH:38]=[CH:37][C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[N:30]=5)[N:26]=[C:8]4[C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[N:12][CH:11]=3)=[CH:14][CH:15]=2)=[N:22][CH:40]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178506484HCID 178506484, compound

Product 1

HCID 86345983HCID 86345983, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of compound 5a (180 mg, 0.370 mmol) in formic acid (3 mL) was stirred in a 10 mL sealed tube at 100° C. for 2 h. After cooling to rt, water (20 mL) was added, and the pH of the solution was adjusted to 7 with saturated NaHCO3 solution. The resulting solids were collected by filtration and washed with Et2O to obtain the title compound 91 as a yellow solid (37 mg, 19% yield). 1H-NMR (300 MHz, DMSO-d6+D2O) δ (ppm): 8.96 (s, 1H), 8.72 (d, J=8.4 Hz, 1H), 8.38-8.32 (m, 4H), 8.19-8.06 (m, 4H), 8.01-7.91 (m, 1H), 7.74-7.68 (m, 2H), 7.58 (s, 1H), 4.45-4.25 (m, 4H), 3.90-3.70 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H23N9O: 502.2 (M+H). Found 502.3.

Workup

  1. customsealed tube at 100° C. for 2 h
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-b9c074aabab54a24ba777d1a34a37dd9
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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