2-chloro-N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-4-pyrimidineamine → N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-[2,3-dihydro-2-(methoxycarbonyl)benzofuran-5-yl]-2,4-primidinediamine

HRID 1475101Notes

Reaction equation

HRID 1475101 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[C:11]([Cl:20])[CH:10]=2)[C:5]([F:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]2[O:30][CH:29]([C:31]([O:33][CH3:34])=[O:32])[CH2:28][C:27]=2[CH:35]=1>>[Cl:20][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[C:5]([F:21])=[CH:4][N:3]=[C:2]([NH:22][C:23]3[CH:24]=[CH:25][C:26]4[O:30][CH:29]([C:31]([O:33][CH3:34])=[O:32])[CH2:28][C:27]=4[CH:35]=3)[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][C:16]([F:19])([F:18])[F:17]

Participants

3

Reactant 2

HCID 220604622-chloro-N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-4-pyrimidineamineHCID 22060823Methyl 5-amino-2,3-dihydrobenzofuran-2-carboxylate

Product 1

HCID 10174439N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-[2,3-dihydro-2-(methoxycarbonyl)benzofuran-5-yl]-2,4-primidinediamine

Procedure

In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-4-pyrimidineamine and 5-amino-2,3-dihydro-2-(methoxycarbonyl)benzofuran were reacted to produce N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-[2,3-dihydro-2-(methoxycarbonyl)benzofuran-5-yl]-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.99 (bs, 1H), 9.49 (bs, 1H), 8.18 (d, 1H, J=4.5 Hz), 8.08 (t, 1H, J=2.4 Hz), 7.81-7.74 (m, 1H), 7.49 (d, 1H, J=8.1 Hz), 7.42 (s, 1H), 7.20 (d, 1H, J=8.1 Hz), 6.78 (d, 1H, J=8.7 Hz), 5.36 (m, 1H), 3.80-3.47 (m, 4H), 3.20 (dd, 1H, J=6.0 and 16.5 Hz); LCMS: purity: 100%; MS (m/e): 500(MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d8ba80e5aa244f6ba375a0d68f1230ec
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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