Trifluoroacetic acid → HCID 136355294, compound

HRID 1262356Notes

Reaction equation

C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[N:21]2[C:16]([CH:17]=[N:18][C:19](S(C)=O)=[N:20]2)=[CH:15][CH:14]=1)=O)(C)(C)C.[NH2:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[NH:29][C:30](=[O:32])[CH3:31].C(O)(C(F)(F)F)=O>>[NH:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[N:21]2[C:16]([CH:17]=[N:18][C:19]([NH:25][C:26]3[CH:27]=[C:28]([NH:29][C:30](=[O:32])[CH3:31])[CH:33]=[CH:34][CH:35]=3)=[N:20]2)=[CH:15][CH:14]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7604m-Aminoacetanilide

HCID 66712404HCID 66712404, compound

Product 1

HCID 136355294HCID 136355294, compound

Procedure

Following the synthetic and purification procedures described in Example 1291c, 2-(2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-pyrrole-1-carboxylic acid tert-butyl ester (80 mg, 0.2 mmol) was coupled with 3′-aminoacetanilide (77.0 mg, 0.513 mmol). Yield of TFA salt: 6 mg (7%); LC/MS: 333 (M+H); HPLC: 97% pure, RT=2.32 min; 1H NMR (DMSO, δ): 11.35 (s, 1H), 9.90 (s, 1H), 9.34 (s, 1H), 8.85 (s, 1H), 7.89 (s, 1H), 7.51 (d, J=8.5, 1H), 7.25 (t, J=8.2, 1H), 7.17 (s, 1H), 7.14 (d, J=4.7, 1H), 7.07 (s, 1H), 6.96 (m, 1H), 6.92 (d, J=4.7, 1H), 6.22 (m, 1H), 2.05 (s, 3H).

Workup

custompurification procedures

Sources & evidence

ORD record: ord-dfc61f8a81ca466dbf4035f6342f24c6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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