Bicarbonate Ion → HCID 178458169, compound

HRID 1046379Notes

Reaction equation

HRID 1046379 reaction equation
C([O:5][C:6]1[C:11]([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[CH:16][C:15]=2[C:24]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)=O)=[CH:10][CH:9]=[CH:8][N:7]=1)(C)(C)C.[O-]C#[N:37].[Na+].C(OCC)(=O)C.[C:45](=[O:48])(O)[O-]>C(O)(=O)C>[OH:5][C:6]1[C:11]([CH2:12][N:13]2[C:14]3[C:15](=[CH:16][C:17]([O:20][CH2:21][C:22]#[CH:23])=[CH:18][CH:19]=3)[C:24]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[N:37][C:45]2=[O:48])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 8857Ethyl AcetateHCID 517096Sodium CyanateHCID 86604384HCID 86604384, compound

Product 1

HCID 178458169HCID 178458169, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 290 mg (0.635 mmol) of {2-[(2-tert-butoxy-pyridin-3-ylmethyl)-amino]-5-propargyloxy-phenyl}-(4-isopropyl-phenyl)-methanone and in 7 ml acetic acid is reacted with 50 mg (0.762 mmol) sodium cyanate. After stirring overnight the mixture is distributed between ethyl acetate and aqueous bicarbonate solution. The organic layer is concentrated to yield the title compound in the form of a yellow solid. m.p. 121-123° C.

Workup

  1. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-2b109eb401ef4eb0aa257206b7886fe3
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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