1H-Indazole → {5-[5-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-amine

HRID 1754681Notes

Reaction equation

HRID 1754681 reaction equation
C(OC(=O)[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.BrC1C=C2C(CC3C=CC(NCC4C=CC(Cl)=CC=4)=NC=3)=CNC2=NC=1.[N:54]1([CH2:60][CH2:61][O:62][C:63]2[CH:64]=[C:65]3[CH:71]=[CH:70][NH:69][C:66]3=[N:67][CH:68]=2)[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1.N1C2C(=CC=CC=2)C=N1.COC1C=C2C(=NC=1)NC=C2.ClC1C=C2C(=NC=1)NC=C2>>[N:54]1([CH2:60][CH2:61][O:62][C:63]2[CH:64]=[C:65]3[C:71]([CH2:25][C:22]4[CH:23]=[CH:24][C:19]([NH:7][CH2:8][C:9]5[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=5)=[N:20][CH:21]=4)=[CH:70][NH:69][C:66]3=[N:67][CH:68]=2)[CH2:55][CH2:56][O:57][CH2:58][CH2:59]1

Participants

7

Reactant 6

HCID 92211H-IndazoleHCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridineHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 595932655-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridineHCID 59593275(5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl esterHCID 59593278[5-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-benzyl)-amine

Product 1

HCID 59593302{5-[5-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-amine

Procedure

Additional compounds may be prepared using steps 3 and 4 of Scheme 32, using (5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester 19 or replacing it with (5-Formyl-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester (43, prepared as described in Example 17) and replacing 5-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridine 79 with an appropriate azaindole, prepared as in Example 29 or 5-methoxy-7-azaindole (prepared as described in Example 31) or with commercially available 5-chloro-7-azaindole. The following compounds were made following this procedure:

Workup

  1. customAdditional compounds may be prepared

Sources & evidence

ORD record
ord-49b3dcd47b2f478abcb6093b02886d1a
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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