2-(Dimethylamino)acetohydrazide → HCID 178483338, compound

HRID 1273018Notes

Reaction equation

C(O[N:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:16]=[C:17]([C:21]([NH:23][CH2:24][CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]2)=[O:22])[CH:18]=[CH:19][CH:20]=1)C.[NH2:32][NH:33][C:34](=O)[CH2:35][N:36]([CH3:38])[CH3:37].C[O-].[Na+]>CO>[CH3:37][N:36]([CH2:35][C:34]1[N:4]=[C:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[C:15]2[CH:16]=[C:17]([C:21]([NH:23][CH2:24][CH2:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]3)=[O:22])[CH:18]=[CH:19][CH:20]=2)[NH:32][N:33]=1)[CH3:38]

Participants

Conditions

Temperature: 105 °C

Procedure

To a suspension of (3-[5-(ethoxyiminomethyl)(1H-indazol-3-yl)]phenyl)-N-(2-piperidylethyl)carboxamide.3HCl (412 mg, 0.78 mmol) and N-amino-2-(dimethylamino)acetamide (275 mg, 2.35 mmol) in anhydrous methanol (5.0 mL) in a screw-top pressure tube was added sodium methoxide (626 mL of a 25% w/w in methanol). The tube was sealed, heated in a 105° C. oil bath for 48 h and then concentrated to dryness. Purification of the residue by preparatory TLC using 40% ethyl acetate in methanol gave the desired product after precipitation from methanol/ethyl acetate with ethyl ether (12 mg, 3% yield) 1H NMR (DMSO-d6) δ 13.7 (br s, 1H), 8.7 (br s, 2H), 8.4 (s, 1H), 8.1–8.0 (m, 2H), 7.85 (br d, 1H), 7.7–7.6 (m, 2H), 3.6 (s, 2H), 3.5–3.3 (m, 2H), 2.5–2.2 (m, 6H), 2.2 (s, 6H), 1.6–1.3 (m, 6H); ES-MS (m/z) 473 [M+H]+.

Workup

customThe tube was sealed
concentrationconcentrated to dryness
customPurification of the residue by preparatory TLC

Sources & evidence

ORD record: ord-262a73cebcff47ce957caca0ce692fd1
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208513B2

Reaction notes

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