1,4-Benzodioxan-6-ylamine → HCID 66758840, compound

HRID 1932073Notes

Reaction equation

HRID 1932073 reaction equation
C1COC2C=[CH:6][C:5]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19]C4C=CC=C(O)C=4)[N:13]=3)=CC=2O1.ClC1N=C(NCC[S:37][CH2:38][C:39]2[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=2[Cl:46])C(F)=CN=1.[O:48]1C2C=CC(N)=CC=2[O:51][CH2:50][CH2:49]1>>[Cl:46][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]([F:45])[C:39]=1[CH2:38][S:37][CH2:6][CH2:5][NH:11][C:12]12[O:51][CH2:50][CH2:49][O:48][N:13]1[C:14]([NH2:19])=[N:15][CH:16]=[C:17]2[F:18]

Participants

4

Reactant 3

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220611812-chloro-N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-4-pyrimidineamine

Product 1

HCID 66758840HCID 66758840, compound

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-4-pyrimidineamine and 1,4-benzodioxan-6-amine were reacted to yield N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-N2-(3,4-ethylenedioxy)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.09 (bs, 1H), 7.94 (bs, 1H), 7.87 (d, 1H, J=4.2 Hz), 7.34-7.30 (m, 2H), 7.24-7.18 (m, 2H), 7.01 (dd, 1H, J=2.4 and 8.7 Hz), 6.68 (d, 1H, J=8.7 Hz), 4.11 (s, 4H), 3.83 (d, 2H, J=1.2 Hz), 3.63-3.56 (m, 2H), 2.74 (t, 2H, J=7.5 Hz); LCMS: ret. time: 25.17 min.; purity: 92%; MS (m/e): 466 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e0c9e47255e444f38676ce01dea56d5a
Source dataset
uspto-grants-2012_05
Patent number
US08188276B2

Reaction notes

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