Cyclopropylboronic acid → HCID 70674930, compound

HRID 1468684Notes

Reaction equation

HRID 1468684 reaction equation
Br[C:2]1SC2C=C(OC)C(C)=CC=2N=1.C1(C2SC3C=C(OC)C(C)=CC=3N=2)CC1.C1(B(O)O)CC1.COC1C(C)=CC2N=CSC=2C=1.[C:47]([O:51][C@@H:52]([C:56]1[C:64]([CH3:65])=[CH:63][C:59]2[N:60]=[CH:61][S:62][C:58]=2[C:57]=1[C:66]1[CH:71]=[CH:70][C:69]([Cl:72])=[CH:68][CH:67]=1)[C:53]([OH:55])=[O:54])([CH3:50])([CH3:49])[CH3:48]>>[C:47]([O:51][C@@H:52]([C:56]1[C:64]([CH3:65])=[CH:63][C:59]2[N:60]=[C:61]([CH3:2])[S:62][C:58]=2[C:57]=1[C:66]1[CH:67]=[CH:68][C:69]([Cl:72])=[CH:70][CH:71]=1)[C:53]([OH:55])=[O:54])([CH3:50])([CH3:48])[CH3:49]

Participants

6

Reactant 5

HCID 2760897Cyclopropylboronic acidHCID 19385238HCID 19385238, compoundHCID 70674929HCID 70674929, compoundHCID 70981883HCID 70981883, compoundHCID 71003635HCID 71003635, compound

Product 1

HCID 70674930HCID 70674930, compound

Procedure

Compound 7 was synthesized from compound 6A according to the procedure used to prepare compound 6B (except that trimethylboxine was used instead of cyclopropyl boronic acid) followed by the procedures to convert compound 5B to compound 5L as outlined in Example 1. 1H-NMR: 400 MHz, (CD3OD) δ: 7.69 (s, 1H), 7.65-7.51 (m, 4H), 5.22 (s, 1H), 2.76 (s, 3H), 2.57 (s, 3H), 0.94 (s, 9H). LCMS-ESI+: calc'd for C21H18ClNO3: 404.1 (M+H+). Found: 404.1 (M+H+).

Sources & evidence

ORD record
ord-42561a983539400d803108cd81acaed5
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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