Dimethylamine → HCID 86656842, compound

HRID 410880Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([NH:13][C:14]3([C:17](O)=[O:18])[CH2:16][CH2:15]3)=[O:12])=[CH:10][C:5]=2[N:4]=[C:3]1[NH:20][C:21]1[S:22][C:23]2[CH:29]=[C:28]([O:30][C:31]([F:34])([F:33])[F:32])[CH:27]=[CH:26][C:24]=2[N:25]=1.[CH3:35][NH:36][CH3:37].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH3:35][N:36]([CH3:37])[C:17]([C:14]1([NH:13][C:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3]([NH:20][C:21]4[S:22][C:23]5[CH:29]=[C:28]([O:30][C:31]([F:34])([F:32])[F:33])[CH:27]=[CH:26][C:24]=5[N:25]=4)=[N:4][C:5]=3[CH:10]=2)=[O:12])[CH2:15][CH2:16]1)=[O:18]

Participants

Reactant 4

HCID 674Dimethylamine

HCID 81531Diisopropylethylamine2×

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 58397772HCID 58397772, compound

Product 1

HCID 86656842HCID 86656842, compound

Conditions

Temperature: 0 °C

Procedure

1-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzimidazole-5-carboxylic acid (1-dimethylcarbamoyl-cyclopropyl)-amide (48 mg) was prepared by following General Procedure F using 1-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzimidazole-5-carbonyl]-amino}-cyclopropanecarboxylic acid (49 mg), dimethyl amine (0.3 ml, 1.0 M solution in THF), HBTU (38 mg), and DIEA (0.1 ml), with a minor modification of General Procedure F where DIEA was slowly added to the reaction mixture at last while stirring at 0° C. LC/MS: m/z 520 [M+2]. 1H NMR (DMSO-d6, 400 MHz): δ 8.92 (s, 1H), 8.06 (s, 1H), 7.91 (m, 1H), 7.72 (d, 1H), 7.60 (br, 1H), 7.46 (d, 1H), 7.33 (d, 1H), 7.24 (m, 1H), 3.66 (s, 3H), 2.87 (d, 6H), 1.26 (t, 2H), and 1.01 (t, 2H).

Sources & evidence

ORD record: ord-9f745280744d46fa872aefd8623a974c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759535B2

Reaction notes

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