Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 59023735, compound

HRID 1678229Notes

Reaction equation

CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.O1CCCCC1[O:24][CH2:25][CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:30]=[C:31]([NH:38][C:39]2[CH:44]=[CH:43][N:42]=[C:41]([NH2:45])[N:40]=2)[CH:32]=[C:33]2[C:37]=1[NH:36][N:35]=[CH:34]2>CO.CCOC(C)=O>[NH2:45][C:41]1[N:40]=[C:39]([NH:38][C:31]2[CH:32]=[C:33]3[C:37](=[C:29](/[CH:28]=[CH:27]/[CH2:26][CH2:25][OH:24])[CH:30]=2)[NH:36][N:35]=[CH:34]3)[CH:44]=[CH:43][N:42]=1

Participants

Conditions

Temperature: 25 °C

Procedure

PPTS (0.019 g, 0.075 mmol) was added to a mixture of 4-{7-[(E)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-1H-indazol-5-ylamino}-pyrimidine-2-amine (prepared from Example #N.2.7 reacted with trans-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyoxy]-tetrahydropyran using general procedure F, 0.037 g, 0.100 mmol) in MeOH (3.0 mL). The reaction mixture was stirred at about 25° C. for about 5 hours. The reaction mixture was diluted with EtOAc (5 mL) and was washed with aqueous Na2CO3 solution (5 mL). The organic portion was evaporated under reduced pressure to afford (E)-4-[5-(2-amino-pyrimidin-4-ylamino)-1H-indazol-7-yl]-but-3-en-1-ol (0.015 g, 0.051 mmol) as an off white solid; RP-HPLC (Table 1, Method e) Rt 0.62 min; m/z: (M+H)+ 297.0.

Workup

washwas washed with aqueous Na2CO3 solution (5 mL)
customThe organic portion was evaporated under reduced pressure

Sources & evidence

ORD record: ord-c306f76275c343bd98f8ca44ad487a1b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008481B2

Reaction notes

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