Trifluoroacetic acid → HCID 137231117, compound

HRID 526119Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]3[CH2:25][CH2:24][CH:23]([N:26](C)[C:27](=O)OC(C)(C)C)[CH2:22]3)=[N:19][CH:20]=1)=[N:11][C:10]([C:35]1[CH:40]=[C:39]([Cl:41])[C:38]([OH:42])=[C:37]([Cl:43])[CH:36]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[ClH:41].[ClH:41].[ClH:41].[Cl:41][C:39]1[CH:40]=[C:35]([C:10]2[N:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[C:13]3[NH:14][C:15]2[CH:20]=[N:19][C:18]([N:21]3[CH2:25][CH2:24][CH:23]([NH:26][CH3:27])[CH2:22]3)=[CH:17][CH:16]=2)[CH:36]=[C:37]([Cl:43])[C:38]=1[OH:42]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 136927272HCID 136927272, compound

Product 1

HCID 137231117HCID 137231117, compoundYield 196.9%

Procedure

Following general procedure D-1, tert-butyl 1-{5-[3-acetyl-6-(3,5-dichloro-4-hydroxy-phenyl)-1,5-naphthyridin-4-ylamino]pyridin-2-yl}pyrrolidin-3-yl(methyl)carbamate (0.183 mmol) was reacted with TFA (2 mL) followed by formation of the trihydrochloride salt to afford the desired product (57 mg, 49% over two steps) as an orange-yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.37 (s, 1H), 8.49 (d, J=8.9 Hz, 1H), 8.40 (d, J=8.9 Hz, 1H), 8.24 (d, J=2.5 Hz, 1H), 7.88 (dd, J=9.4, 2.5 Hz, 1H), 7.57 (s, 2H), 6.96 (d, J=9.4 Hz, 1H), 4.13-4.00 (m, 2H), 3.92-3.79 (m, 2H), 3.66-3.73 (m, 1H), 2.83 (s, 6H), 2.72-2.60 (m, 1H), 2.45-2.34 (m, 1H); ESI MS m/z 523 [M+H]+; HPLC>99% (AUC), tR=8.97 min.

Sources & evidence

ORD record: ord-2e69b62d65c54581a50864ceba9fad68
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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