Reserpine → HCID 178422920, compound

HRID 51584Notes

Reaction equation

HRID 51584 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:22]4[C:21](Cl)=[N:20][CH:19]=[N:18][C:17]=4[N:16]([C@H:24]4[CH2:29][CH2:28][C@H:27]([N:30]5[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]5)[CH2:26][CH2:25]4)[CH:15]=3)=[CH:10][C:9]=2[CH3:37])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.COC1C=C(C2C3C(N)=NC=NC=3[N:59]([C@H]3CC[C@H](N4CCN(C)CC4)CC3)C=2)C=CC=1OC1C=CC=CC=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[CH3:37][C:9]1[CH:10]=[C:11]([C:14]2[C:22]3[C:21]([NH2:59])=[N:20][CH:19]=[N:18][C:17]=3[N:16]([C@H:24]3[CH2:29][CH2:28][C@H:27]([N:30]4[CH2:31][CH2:32][N:33]([CH3:36])[CH2:34][CH2:35]4)[CH2:26][CH2:25]3)[CH:15]=2)[CH:12]=[CH:13][C:8]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5770ReserpineHCID 178422919HCID 178422919, compoundHCID 178476643HCID 178476643, compound

Product 1

HCID 178422920HCID 178422920, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared in a 75% yield from trans-4-{4-chloro-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-methylphenyl phenyl ether in a similar manner to that described for the preparation of trans-5-(3-methoxy-4-phenoxyphenyl)-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine acetate: 1H NMR (DMSO-d6, 400 MHz) δ 8.13(s, 1H), 7.42(m, 4H), 7.37(t, 2H), 7.27(m, 1H), 7.10 (t, 1H), 6.97(m, 3H), 6.11(bs, 2H), 4.55(m, 1H), 2.2-2.6(m, 9H), 2.22(s, 3H), 2.14 (s, 3H), 1.7-2.0(m, 6H), 1.45(m, 2H); MS MH+497.4; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 5%-100% acetonitrile—0.05 M ammonium acetate over 25 min, 1 ml/min) tr 15.93 min.

Workup

  1. customtr 15.93 min.

Sources & evidence

ORD record
ord-3af11ab478034ab0b04d406433ebd822
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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