Phosgene → 3-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-1-(6-methyl-pyridin-3-ylmethyl)-urea

HRID 1063003Notes

Reaction equation

HRID 1063003 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[C:7]([O:17][CH3:18])[C:5]=2[N:6]=1.[C:19](Cl)(Cl)=[O:20].[CH3:23][NH:24][CH2:25][C:26]1[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=1>>[CH3:18][O:17][C:7]1[C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:20])[N:24]([CH3:23])[CH2:25][C:26]3[CH:27]=[N:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[S:3][C:4]=2[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amineHCID 154773072-Methyl-5-[(methylamino)methyl]pyridine

Product 1

HCID 222831933-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-1-(6-methyl-pyridin-3-ylmethyl)-ureaYield 25%

Procedure

Conversion of 2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol (100 mg, 0.377 mg) with phosgene (20% in toluene, 0.2 ml) and methyl-(6-methyl-pyridin-3-ylmethyl)-amine (0.064 ml, 0.47 mmol) using the general procedure D affords the product as white solid in 25% yield. MS: m/e=429 (M+H+).

Sources & evidence

ORD record
ord-ea74215d3ca44728803d15c7e8e55b88
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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