tert-Butyl piperazine-1-carboxylate → HCID 69219755, compound

HRID 902467Notes

Reaction equation

HRID 902467 reaction equation
C(OC([C:6]1[S:7][CH:8]=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH:11]=[C:10]2Cl)=O)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[CH2:17]([O:21][C:22]([C:11]1[C:12](=[O:15])[NH:13][C:14]2[C:9]([C:10]=1[N:27]1[CH2:28][CH2:29][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:23])[CH2:25][CH2:26]1)=[CH:8][S:7][CH:6]=2)=[O:23])[CH3:18]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 69150786HCID 69150786, compound

Product 1

HCID 69219755HCID 69219755, compound

Procedure

In another method, intermediate 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-3-carboxylic acid ethyl ester, depicted by formula (25), was reacted with tert-butyl-1-piperazine carboxylate to yield 7-(4-tert-butoxycarbonyl-piperazin-1-yl)-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester, depicted by formula (28). This intermediate was either reacted with an appropriate halide (R1—X) or boronic acid (R1—B(OH)2) to yield an intermediate of structure (29), which was deprotected and reacted with an appropriate acid chloride (R3—COCl) or acid (R3—COOH) to yield target compounds of structure (II), with R2 as ethyl carboxylate, and R1 and R3 as defined above, as shown in Scheme 14.

Sources & evidence

ORD record
ord-7c4b583ba6b042749ba80dc878b9d115
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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