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 1256753Notes

Reaction equation

HRID 1256753 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.C(OC(=O)N(CC1C=CC(Cl)=CC=1)C1C=CC(C=O)=CN=1)(C)(C)C.[N:52]1([CH2:58][CH2:59][O:60][C:61]2[CH:62]=[C:63]3[CH:69]=[CH:68][NH:67][C:64]3=[N:65][CH:66]=2)[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.N1C2C(=CC=CC=2)C=N1.COC1C=C2C(=NC=1)NC=C2.ClC1C=C2C(=NC=1)NC=C2>>[N:52]1([CH2:58][CH2:59][O:60][C:61]2[CH:62]=[C:63]3[C:69]([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:68][NH:67][C:64]3=[N:65][CH:66]=2)[CH2:53][CH2:54][O:55][CH2:56][CH2:57]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 59593313(4-Chloro-benzyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester

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-c178f7b335f34ad59f81122bc0c99020
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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