1-Isopropylpiperazine → HCID 86700282, compound

HRID 879469Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:7]2[S:8][C:9]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)=[C:14]([C@H:23]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:24]([O:26][CH3:27])=[O:25])[C:13]([CH3:33])=[CH:12][C:10]=3[N:11]=2)[S:5][CH:6]=1.[CH:34]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([CH3:36])[CH3:35]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[OH-].[K+].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[C:29]([O:28][C@@H:23]([C:14]1[C:13]([CH3:33])=[CH:12][C:10]2[N:11]=[C:7]([C:4]3[S:5][CH:6]=[C:2]([N:40]4[CH2:41][CH2:42][N:37]([CH:34]([CH3:36])[CH3:35])[CH2:38][CH2:39]4)[N:3]=3)[S:8][C:9]=2[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:24]([O:26][CH3:27])=[O:25])([CH3:32])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 105 °C

Procedure

In a 5 mL microwave reaction tube, (S)-methyl 2-(2-(4-bromothiazol-2-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (50 mg, 0.08 mmol), isopropylpiperazine (34 mg, 3 eq.), Bis(tri-t-butylphosphine)palladium(0) (3 mg, 15%), cetyltrimethylammonium bromide (4 mg, 0.5 eq.) were charged with 1 mL toluene, then 1 drop of 50% KOH aqueous solution (excess) was added. The reaction was heated to 105° C. for 1 hour. Reaction mixture was purified by HPLC (0.1% TFA in ACN and water) to give desired product. LCMS-ESI+: calc'd for C31H38ClN4O3S2: 613.2 (M+H+); Found: 613.4 (M+H+).

Workup

customReaction mixture
customwas purified by HPLC (0.1% TFA in ACN and water)

Sources & evidence

ORD record: ord-0c6bb3df8ff3469eabf423ce2a0b9443
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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