Sodium Bicarbonate → HCID 67215455, compound

HRID 1630733Notes

Reaction equation

[OH:1][C@@H:2]([CH2:24][OH:25])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[C:15]([SH:19])[N:14]=[C:13]([O:20][CH3:21])[C:12]=2[C:22]#[N:23])=[CH:7][CH:6]=1.Cl[CH2:27][C:28]1[N:29]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[S:31][CH:32]=1.C(=O)(O)[O-].[Na+]>>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([C:30]2[S:31][CH:32]=[C:28]([CH2:27][S:19][C:15]3[C:16]([C:17]#[N:18])=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][C@@H:2]([OH:1])[CH2:24][OH:25])=[CH:6][CH:7]=4)[C:12]([C:22]#[N:23])=[C:13]([O:20][CH3:21])[N:14]=3)[N:29]=2)=[CH:38][CH:37]=1

Participants

Reactant 3

HCID 516892Sodium Bicarbonate

HCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole

HCID 178494292HCID 178494292, compound

Product 1

HCID 67215455HCID 67215455, compound

Procedure

The solution from Example 29A is stirred together with 75 mg (0.306 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 93 mg (1.112 mmol) of sodium bicarbonate at room temperature overnight. The reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added). This gives 33 mg (20% of theory over two steps) of the target compound.

Workup

customThe reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% TFA added)

Sources & evidence

ORD record: ord-67abff44122d4375b577491ae300d171
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791146B2

Reaction notes

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