1-Bromopropane → HCID 178459273, compound

HRID 731480Notes

Reaction equation

HRID 731480 reaction equation
C1(N(C2CCCCC2)C(=O)NC2SC(S(NC[C:20](O)=[O:21])(=O)=O)=CN=2)CCCCC1.[CH:30]1([NH:36][C@H:37]2[CH2:42][CH2:41][C@H:40]([O:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:38]2)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C1(N([C@H]2CC[C@H](OC)CC2)C(=O)NC2SC(SCC(O)=O)=CN=2)CCCC1.O[C@H]1CC[C@H](C2C=CC=C3C=2C(=O)NC3=O)CC1.BrCCC.C1(=O)CCCCC1.C[O:104][C:105](=[O:119])[C:106]([NH:109][S:110]([C:113]1[S:117][C:116]([NH2:118])=[N:115][CH:114]=1)(=[O:112])=[O:111])([CH3:108])[CH3:107]>>[CH:30]1([N:36]([C@H:37]2[CH2:42][CH2:41][C@H:40]([O:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:38]2)[C:20](=[O:21])[NH:118][C:116]2[S:117][C:113]([S:110]([NH:109][C:106]([CH3:108])([CH3:107])[C:105]([OH:104])=[O:119])(=[O:112])=[O:111])=[CH:114][N:115]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

8

Reactant 7

HCID 78401-BromopropaneHCID 7967CyclohexanoneHCID 57688273N-{2-[(Dicyclohexylcarbamoyl)amino]-1,3-thiazole-5-sulfonyl}glycineHCID 866301962-(2-Amino-thiazole-5-sulfonylamino)-2-methyl-propionic acid methyl esterHCID 178459265HCID 178459265, compoundHCID 178496618HCID 178496618, compoundHCID 178518244HCID 178518244, compound

Product 1

HCID 178459273HCID 178459273, compound

Procedure

Prepared in a similar manner to [2-(3,3-dicyclohexyl-ureido)-thiazole-5-sulfonylamino]-acetic acid via cyclohexyl-(trans-4-propoxy-cyclohexyl)-amine (prepared according to the procedure described for the synthesis of {2-[3-cyclopentyl-3-(trans-4-methoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid (Step 1) using (trans-4-hydroxy-cyclohexyl)-isoindole-1,3-dione, 1-bromopropane and cyclohexanone) and 2-(2-amino-thiazole-5-sulfonylamino)-2-methyl-propionic acid methyl ester to give the title compound.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-475b6146efc240dfb45314e6b8052f4a
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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