1,1,3,3-Tetramethylguanidine → HCID 68466355, compound

HRID 1177673Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5](P(OC)(OC)=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].CN(C)C(=N)N(C)C.[C:31]([O:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][C:43]([CH:47]=O)=[CH:44][CH:45]=2)[CH:40]=[N:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>O1CCCC1>[C:31]([O:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][C:43]([CH:47]=[C:5]([NH:6][C:7]([O:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:8])[C:3]([O:2][CH3:1])=[O:4])=[CH:44][CH:45]=2)[CH:40]=[N:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-(benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (5.50 g, 16.6 mmol) and tetramethylguanidine (1.99 mL, 15.9 mmol) in anhydrous tetrahydrofuran (50 mL) was stirred at −78° C. for 20 min. To this was added a solution of 5-formyl-indazole-1-carboxylic acid tert-butyl ester (3.72 g, 15.1 mmol) in tetrahydrofuran (25 mL) slowly via syringe over 10 min. The reaction mixture was stirred at −78° C. for 4 h and then allowed to warm to room temperature overnight. The solvent was evaporated and the resulting residue subjected to flash column chromatography on silica gel (1:2 ethyl acetate/hexane) giving the title compound as a white foam (5.77 g, 85%). 1H-NMR (CDCl3, 500 MHz) δ 8.09 (d, J=9.0 Hz, 1H), 8.08 (s, 1H), 7.84 (s, 1H), 7.67 (d, J=9.0 Hz, 1H), 7.47 (s, 1H), 7.30 (br s, 5H), 6.43 (br s, 1H), 5.09 (s, 2H), 3.84 (s, 3H), 1.72 (s, 9H). Mass spec.: 452 (MH)+.

Workup

temperatureto warm to room temperature overnight
customThe solvent was evaporated

Sources & evidence

ORD record: ord-aefd6dcd0fbc4d24baceabef049c003f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842808B2

Reaction notes

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