Reserpine → HCID 178480938, compound

HRID 51577

Reaction equation

HRID 51577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ClC1C2C(I)=CN([C@H]3CC[C@H](N4CCN(C)CC4)CC3)C=2N=CN=1.[NH2:48][C:49]1[C:50]2[C:57](C3C=CC(OC4C=CC=CC=4)=C(C=3)C#N)=[CH:56][N:55]([C@H:73]3[CH2:78][CH2:77][C@H:76]([N:79]4[CH2:84][CH2:83][N:82]([CH3:85])[CH2:81][CH2:80]4)[CH2:75][CH2:74]3)[C:51]=2[N:52]=[CH:53][N:54]=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>[Cl:1][C:2]1[CH:3]=[C:4]([C:57]2[C:50]3[C:49]([NH2:48])=[N:54][CH:53]=[N:52][C:51]=3[N:55]([C@H:73]3[CH2:78][CH2:77][C@H:76]([N:79]4[CH2:84][CH2:83][N:82]([CH3:85])[CH2:81][CH2:80]4)[CH2:75][CH2:74]3)[CH:56]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 5770ReserpineHCID 227362172-(3-Chloro-4-phenoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178480940HCID 178480940, compoundHCID 178480946HCID 178480946, compound

Product 1

HCID 178480938HCID 178480938, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from 2-(3-chloro-4-phenoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and trans-4-chloro-5-iodo-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidine in a similar manner to that described for the preparation of trans-5-{4-amino-7-[4-(4-methylpiperazino)cyclohexyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-2-phenoxybenzonitrile: 1H NMR (DMSO-d6, 400 MHz) δ 8.14 (s, 1H), 7.79(s, 1H), 7.65 (s, 1H), 7.38(m, 3H), 7.16(t, 2H), 7.04 (d, 2H), 6.24(bs, 2H), 4.55(m, 1H), 2.2-2.6(m, 9H), 2.16(s, 3H), 1.89(m, 6H), 1.48 (m, 2H); MS MH+517.3; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 15.75 min.

Workup

  1. customtr 15.75 min.

Sources & evidence

ORD record
ord-3ad3ec14c5514985a4b56946f39a3c5a
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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