Trifluoroacetic acid → [4-Chloro-3-((R)-1-pyrrolidin-2-ylmethoxy)-phenyl]-[7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262181Notes

Reaction equation

C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:20][O:21][C:22]1[CH:27]=[C:26]([NH:28][C:29]2[N:34]=[CH:33][C:32]3=[CH:35][CH:36]=[C:37]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([S:44]([CH3:47])(=[O:46])=[O:45])[CH:39]=4)[N:31]3[N:30]=2)[CH:25]=[CH:24][C:23]=1[Cl:48])=O)(C)(C)C>>[Cl:48][C:23]1[CH:24]=[CH:25][C:26]([NH:28][C:29]2[N:34]=[CH:33][C:32]3=[CH:35][CH:36]=[C:37]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([S:44]([CH3:47])(=[O:45])=[O:46])[CH:39]=4)[N:31]3[N:30]=2)=[CH:27][C:22]=1[O:21][CH2:20][C@H:16]1[CH2:17][CH2:18][CH2:19][NH:15]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 66712273(R)-2-{2-Chloro-5-[7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenoxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66712223[4-Chloro-3-((R)-1-pyrrolidin-2-ylmethoxy)-phenyl]-[7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Procedure

This example was made by TFA deprotection of (R)-2-{2-Chloro-5-[7-(3-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenoxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester as described in Example 1223. 1H-NMR (DMSO) δ 9.7 (s, 1H), 9.5 (brs, 1H), 9.0 (s, 1H), 8.7 (brs, 1H), 8.6 (s, 1H), 8.4 (d, J=8.0 Hz, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.8 (t, 1H), 7.6 (d, J=8.7 Hz, 1H), 7.4 (m, 2H), 7.3 (d, J=4.7 Hz, 1H), 7.0 (d, J=4.7 Hz, 1H), 4.1 (m, 1H), 3.95 (m, 2H), 3.3 (s, 3H), 3.2 (m, 2H), 2.0 (m, 2H), 1.9 (m, 1H), 1.7 (m, 1H); LC/MS (ESI+): 498 (M+H).

Sources & evidence

ORD record: ord-d579b5eeaf154502ac2f5b63dd55669d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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