2-[2-(2,6-Dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridine-4-ylamino]-isonicotinonitrile → 3,5-Dichloro-4-{4-[5-(3-hydroxy-azetidin-1-yl)-pyrimidin-4-ylamino]-thiazolo[5,4-c]pyridine-2-yl}-benzonitrile

HRID 2366215Notes

Reaction equation

HRID 2366215 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[S:12][C:13]2[C:14]([NH:20][C:21]3[CH:22]=C(C=[CH:27][N:28]=3)C#N)=[N:15][CH:16]=[CH:17][C:18]=2[N:19]=1.Br[C:30]1C2SC(C3C(Cl)=CC(C#N)=CC=3Cl)=NC=2C=C[N:31]=1.NC1N=CN=C([N:56]2[CH2:59][CH:58]([OH:60])[CH2:57]2)C=1>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:10])[C:3]=1[C:11]1[S:12][C:13]2[C:14]([NH:20][C:21]3[C:22]([N:56]4[CH2:59][CH:58]([OH:60])[CH2:57]4)=[CH:30][N:31]=[CH:27][N:28]=3)=[N:15][CH:16]=[CH:17][C:18]=2[N:19]=1)[C:8]#[N:9]

Participants

4

Reactant 3

HCID 569532942-[2-(2,6-Dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridine-4-ylamino]-isonicotinonitrileHCID 668014651-(6-Aminopyrimidin-4-yl)azetidin-3-olHCID 866689964-(4-Bromothiazolo[5,4-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

Product 1

HCID 569532933,5-Dichloro-4-{4-[5-(3-hydroxy-azetidin-1-yl)-pyrimidin-4-ylamino]-thiazolo[5,4-c]pyridine-2-yl}-benzonitrileYield 52%

Procedure

Following the procedure described for 2-[2-(2,6-dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridine-4-ylamino]-isonicotinonitrile (Example 19), 4-(4-bromo-thiazolo[5,4-c]pyridine-2-yl)-3,5-dichloro-benzonitrile and 1-(6-amino-pyrimidin-4-yl)-azetidin-3-ol were reacted to give the desired compound as a yellow solid (56 mg, 52% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.24 (s, 1H), 8.39 (d, J=5.5 Hz, 1H), 8.37 (s, 2H), 8.20 (d, J=1.0 Hz, 1H), 7.74 (d, J=5.6 Hz, 1H), 6.58 (s, 1H), 5.72-5.69 (m, 1H), 4.63-4.56 (m, 1H), 4.20 (t, J=7.8 Hz, 2H), 3.73 (dd, J=9.1, 4.5 Hz, 2H). LCMS (Method C): RT=3.21, m/z: 470 [M+H+].

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cd2884d410a9460dbf01c40630c7907f
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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