HCID 89971184, compound → HCID 86578319, compound

HRID 1400750Notes

Reaction equation

HRID 1400750 reaction equation
[CH2:1]([O:4][C:5]1([CH3:51])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:26]5[CH:31]=[C:30](Cl)[C:29]([CH3:33])=[CH:28][C:27]=5[O:34][C@H:35]([CH2:37][CH:38]=[CH2:39])[CH3:36])[CH:23]=[CH:24][CH:25]=4)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:40])[C:12]=2[C@H:41]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:42]([O:44]C)=[O:43])[CH2:7][CH2:6]1)C=C.C(OC1(C)CC[N:59](C2N3N=C(C4C=C(C5C(O[C@H](CC=C)C)=CC=C(Cl)C=5C)C=CC=4)C=C3N=C(C)C=2[C@H](OC(C)(C)C)C(OC)=O)CC1)C=C.BrC1C=C(Cl)C(C)=CC=1O[C@H](CC=C)C.BrC1C(C)=C(Cl)C=CC=1O[C@H](CC=C)C>>[C:47]([O:46][C@@H:41]([C:12]1[C:13]([CH3:40])=[N:14][C:15]2=[CH:19][C:18]3=[N:17][N:16]2[C:11]=1[N:8]1[CH2:7][CH2:6][C:5]([CH3:51])([O:4][CH2:1][CH2:39][CH2:38][CH2:37][C@H:35]([CH3:36])[O:34][C:27]2[CH:28]=[C:29]([C:33]#[N:59])[CH:30]=[CH:31][C:26]=2[C:22]2[CH:21]=[C:20]3[CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:9]1)[C:42]([OH:44])=[O:43])([CH3:48])([CH3:49])[CH3:50]

Participants

5

Reactant 4

HCID 89971184HCID 89971184, compoundHCID 89971218HCID 89971218, compound2×HCID 89971238HCID 89971238, compound2×HCID 89971410HCID 89971410, compound

Product 1

HCID 86578319HCID 86578319, compound

Procedure

(S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5′-chloro-4′-methyl-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate and (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3′-chloro-2′-methyl-6′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate: Prepared from a 2:1 mixture of (S)-1-bromo-5-chloro-4-methyl-2-(pent-4-en-2-yloxy)benzene and (S)-2-bromo-4-chloro-3-methyl-1-(pent-4-en-2-yloxy)benzene using the same procedures as intermediate 182 and 168 to provide an inseperable mixture of the products in 98% yield and 2:1 ratio. (S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5′-chloro-4′-methyl-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate. LCMS (M+1)=715.4. (S)-Methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3′-chloro-2′-methyl-6′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate. LCMS (M+1)=715.4.

Workup

  1. customto provide
  2. additionan inseperable mixture of the products in 98% yield and 2:1 ratio

Sources & evidence

ORD record
ord-a1159b5c612842ddb495e5f06adef8cd
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

Loading…