4-(3-Bromophenyl)-1,3-thiazol-2-amine → 8-Nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxamide

HRID 906826Notes

Reaction equation

HRID 906826 reaction equation
C[C:2]1([C:21]([OH:23])=O)[CH2:17][C:10]2([N+:18]([O-:20])=[O:19])[C:11]3[C:16]([CH:3]1[C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.BrC1C=C(C2[N:32]=C(N)SC=2)C=CC=1>>[N+:18]([C:10]12[CH2:17][CH:2]([C:21]([NH2:32])=[O:23])[CH:3]([C:4]3[C:9]1=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:16]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=1)([O-:20])=[O:19]

Participants

3

Reactant 2

HCID 7233304-(3-Bromophenyl)-1,3-thiazol-2-amineHCID 596985749-Nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid

Product 1

HCID 866138978-Nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxamideYield 92.4%

Procedure

In a similar manner to Example 1, Step 2, the coupling reaction of 15-methyl-8-nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylic acid (200 mg, 0.647 mmol) and 4-(3-bromo-phenyl)-thiazol-2-ylamine (214 mg, 0.841 mmol) afforded 15-methyl-N-[4-(3-bromo-phenyl)-thiazol-2-yl]-]-8-nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxamide (176 mg, 49% yield). LC/MS (m/z 548.08 (M+H)+); HPLC Rt: 4.385 min.

Sources & evidence

ORD record
ord-c7bf4c14c1b24d2e94fe6dfa1d742078
Source dataset
uspto-grants-2011_09
Patent number
US08013004B2

Reaction notes

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